Schedule & Results
| Date | Time | Team | Opponent | Home/Away | Location | Event Type |
|---|---|---|---|---|---|---|
| 09/19/2019 | 10:00 | Harriers Jr School | To Be Announced | Home | Trinity College School | Lucky 13 |
| 09/20/2019 | 09:00 | Hockey Sr Girls Div I | Hockey Training Institute | Away | Ridley College | Tournament |
| 09/20/2019 | 14:30 | Football Jr Boys | Campbellford D.H.S. | Away | Campbellford D.H.S. | |
| 09/20/2019 | 16:30 | Hockey Sr Girls Div I | North York Storm | Away | Ridley College | Tournament |
| 09/20/2019 | 18:30 | Basketball Jr Girls Div I | To Be Announced | Away | Adam Scott Collegiate | Tournament |
| 09/21/2019 | 07:30 | Hockey Sr Girls Div I | St. Catherines Jr Badgers | Away | Ridley College | Tournament |
| 09/21/2019 | 10:30 | Basketball Jr Girls Div I | To Be Announced | Away | Adam Scott Collegiate | Tournament |
| 09/21/2019 | 11:00 | Soccer Sr Boys Div I | Appleby | Home | Bigside Soccer Field | CISAA League game |
| 09/21/2019 | 14:00 | Football Sr Boys | Upper Canada College | Home | Hargraft Field | CISAA League game |
| 09/21/2019 | 16:30 | Hockey Sr Girls Div I | Niagara Purple Eagles | Away | Ridley College | Tournament |
| 09/21/2019 | 18:30 | Hockey Sr Boys Div I | Ontario Hockey Academy | Away | Cornwall Benson Centre | Exhibition Game |
| 09/22/2019 | 11:00 | Hockey Sr Boys Div I | Ontario Hockey Academy | Away | P.C.M. Rink | Exhibition Game |
| 09/24/2019 | 10:00 | Field Hockey Jr Girls | Haliburton Highlands S.S. | Away | Peterborough | Tournament |
| 09/24/2019 | 10:30 | Field Hockey Sr Girls Div II | Hagersville | Away | Peterborough | Tournament |
| 09/24/2019 | 13:00 | Field Hockey Jr Girls | Bayview | Away | Peterborough | Tournament |
| 09/24/2019 | 13:30 | Field Hockey Sr Girls Div II | Lakefield District S.S. | Away | Peterborough | Tournament |
| 09/24/2019 | 14:30 | Field Hockey Jr Girls | St. Peter's S.S. | Away | Peterborough | Tournament |
| 09/24/2019 | 15:00 | Field Hockey Sr Girls Div II | Crestwood S.S. | Away | Peterborough | Tournament |
| 09/25/2019 | 08:30 | Golf Sr School | C.I.S.A.A. Schools | Away | Deer Creek GC | |
| 09/25/2019 | 13:30 | Football Jr Boys | North Hastings S.S. | Away | North Hastings H.S. | |
| 09/25/2019 | 13:30 | Harriers Jr School | C.I.S.A.A. Schools | Away | Hillfield Strathallan College | Invitational |
| 09/25/2019 | 14:15 | Soccer Sr Boys Div I | Crescent School | Away | Crescent School | CISAA League game |
| 09/25/2019 | 15:00 | Soccer Jr Boys Div I | Appleby | Away | Appleby College | CISAA League game |
| 09/25/2019 | 15:30 | Basketball Sr Girls Div I | Crestwood Preparatory College | Home | Sue Burns Gym | CISAA League game |
| 09/25/2019 | 15:30 | Basketball Jr Girls Div I | Crestwood Preparatory College | Home | West Gym | CISAA League game |
| 09/25/2019 | 15:30 | Soccer U14 Boys Div III | Holy Trinity School | Away | Holy Trinity School | CISAA League game |
| 09/25/2019 | 16:15 | Field Hockey Sr Girls Div I | Nichols School | Away | Nichols School | CISAA League game |
| 09/26/2019 | 15:30 | Basketball U14 Girls Div III | Montcrest School | Away | Montcrest School | CISAA League game |
| 09/26/2019 | 15:30 | Hockey Sr Boys Div I | Blyth Academy-Burlington | Away | Ridley College | |
| 09/27/2019 | 09:00 | Basketball Jr Girls Div I | To Be Announced | Away | Pauline Johnson Collegiate | Tournament |
| 09/27/2019 | 13:25 | Hockey Sr Boys Div I | A21 Academy | Away | Ridley College | |
| 09/27/2019 | 15:30 | Hockey Jr Boys Div I | Heritage | Away | Montreal | Exhibition Game |
| 09/28/2019 | 10:00 | Hockey Jr Boys Div I | Heritage | Away | Montreal | Exhibition Game |
| 09/28/2019 | 11:00 | Basketball Sr Girls Div I | Ridley College | Away | Ridley College | CISAA League game |
| 09/28/2019 | 11:00 | Field Hockey Sr Girls Div I | St. John's Kilmarnock | Away | St. John's Kilmarnock | CISAA League game |
| 09/28/2019 | 11:00 | Soccer U12 Boys | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 09/28/2019 | 11:50 | Hockey Sr Boys Div I | Academie St. Louis | Away | Ridley College | |
| 09/28/2019 | 12:00 | Soccer U12 Boys | Crescent School | Away | St. Andrew's College | CISAA League game |
| 09/28/2019 | 12:00 | Field Hockey Sr Girls Div II | Appleby | Away | Appleby College | CISAA League game |
| 09/28/2019 | 13:00 | Soccer Sr Boys Div I | De La Salle | Away | De La Salle | CISAA League game |
| 09/28/2019 | 13:00 | Soccer Jr Boys Div I | Lakefield College School | Away | Lakefield College School | Exhibition Game |
| 09/28/2019 | 14:00 | Football Sr Boys | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 09/28/2019 | 14:30 | Field Hockey Jr Girls | Lakefield College School | Away | Lakefield College School | CISAA League game |
| 09/28/2019 | 20:10 | Hockey Sr Boys Div I | Loyola High School | Away | Ridley College | |
| 09/29/2019 | 10:00 | Hockey Sr Boys Div I | Lake Forest Academy | Away | Ridley College | |
| 09/30/2019 | Home | P.C.M. Rink | CISAA League game | |||
| 09/30/2019 | 16:00 | Albert College | Home | Boulden South | Exhibition Game | |
| 10/02/2019 | 15:00 | Field Hockey Jr Girls | Bishop Strachan School | Home | Field Hockey LS | CISAA League game |
| 10/02/2019 | 16:00 | Home | P.C.M. Rink | CISAA League game | ||
| 10/02/2019 | 16:00 | Soccer Sr Boys Div I | St. Michael's College | Home | Bigside Soccer Field | CISAA League game |
| 10/02/2019 | 16:00 | Basketball Sr Girls Div I | Appleby | Home | Sue Burns Gym | CISAA League game |
| 10/02/2019 | 16:15 | Field Hockey Jr Girls | Bishop Strachan School | Home | Field Hockey LS | CISAA League game |
| 10/02/2019 | 16:30 | Field Hockey Sr Girls Div I | Appleby | Home | Field Hockey BS | CISAA League game |
| 10/03/2019 | 14:00 | Soccer U12 Boys | To Be Announced | Away | Holy Trinity School | CISAA League game |
| 10/03/2019 | 15:00 | Soccer U14 Boys Div III | Pickering College | Home | Boulden North | CISAA League game |
| 10/03/2019 | 19:30 | Hockey Jr Boys Div I | Leaside S.S. | Home | P.C.M. Rink | Exhibition Game |
| 10/04/2019 | 09:00 | Harriers Sr School | To Be Announced | Away | Durham Forest | Invitational |
| 10/04/2019 | 15:00 | Football Jr Boys | Norwood D.H.S. | Home | Hay Field | |
| 10/04/2019 | 17:00 | Hockey Sr Girls Div I | West Northumberland | Home | P.C.M. Rink | Exhibition Game |
| 10/04/2019 | 18:45 | Hockey Jr Boys Div I | Somang Hockey | Home | P.C.M. Rink | Exhibition Game |
| 10/04/2019 | 20:15 | Hockey Sr Boys Div I | Somang Hockey | Home | P.C.M. Rink | Exhibition Game |
| 10/05/2019 | 11:00 | Hockey Sr Girls Div I | Vaughan Flames | Home | P.C.M. Rink | Exhibition Game |
| 10/05/2019 | 11:30 | Field Hockey Jr Girls | Lakefield College School | Home | Field Hockey LS | CISAA League game |
| 10/05/2019 | 11:30 | Field Hockey Sr Girls Div II | Lakefield College School | Home | Field Hockey BS | Exhibition Game |
| 10/05/2019 | 11:30 | Basketball U14 Girls Div III | Trafalgar Castle School | Home | Sue Burns Gym | Exhibition Game |
| 10/05/2019 | 12:30 | Hockey Jr Boys Div I | Somang Hockey | Home | P.C.M. Rink | Exhibition Game |
| 10/05/2019 | 13:00 | Soccer Sr Boys Div I | Alumni | Home | Bigside Soccer Field | |
| 10/05/2019 | 13:00 | Basketball Sr Girls Div I | St. Clement's School | Home | Sue Burns Gym | Exhibition Game |
| 10/05/2019 | 13:00 | Basketball Jr Girls Div I | St. Clement's School | Home | West Gym | CISAA League game |
| 10/05/2019 | 13:00 | Field Hockey Sr Girls Div I | Villanova College | Home | Field Hockey BS | CISAA League game |
| 10/05/2019 | 14:00 | Hockey Sr Boys Div I | Somang Hockey | Home | P.C.M. Rink | Exhibition Game |
| 10/05/2019 | 14:00 | Football Sr Boys | Huron Heights | Home | Hargraft Field | CISAA League game |
| 10/05/2019 | 19:30 | Hockey Sr Girls Div I | West Northumberland | Home | P.C.M. Rink | Exhibition Game |
| 10/06/2019 | 09:30 | Hockey Jr Boys Div I | Somang Hockey | Home | P.C.M. Rink | Exhibition Game |
| 10/06/2019 | 11:00 | Hockey Sr Boys Div I | Somang Hockey | Home | P.C.M. Rink | CISAA League game |
| 10/06/2019 | 13:00 | Hockey Sr Girls Div I | To Be Announced | Home | P.C.M. Rink | Exhibition Game |
| 10/07/2019 | 15:30 | Basketball Jr Girls Div I | Branksome Hall | Home | Sue Burns Gym | CISAA League game |
| 10/07/2019 | 16:00 | Hockey Sr Girls Div I | Home | P.C.M. Rink | ||
| 10/08/2019 | 15:00 | Field Hockey Jr Girls | Toronto Montessori School | Home | Field Hockey LS | CISAA League game |
| 10/08/2019 | 15:00 | Basketball U14 Girls Div III | Toronto Montessori School | Home | Sue Burns Gym | CISAA League game |
| 10/08/2019 | 16:00 | Soccer Jr Boys Div I | St. Michael's College | Home | Boulden South | CISAA League game |
| 10/09/2019 | 11:00 | Harriers Sr School | To Be Announced | Away | Lakefield College School | Invitational |
| 10/09/2019 | 14:30 | Basketball U14 Girls Div III | Trafalgar Castle School | Home | Sue Burns Gym | CISAA League game |
| 10/09/2019 | 15:00 | Football Jr Boys | Campbellford D.H.S. | Home | Hay Field | |
| 10/09/2019 | 15:00 | Soccer U14 Boys Div III | St. John's Kilmarnock | Away | St. John's Kilmarnock | CISAA League game |
| 10/09/2019 | 16:00 | Basketball Sr Girls Div I | Havergal College | Home | Sue Burns Gym | CISAA League game |
| 10/09/2019 | 16:00 | Field Hockey Sr Girls Div I | Havergal College | Home | Field Hockey BS | CISAA League game |
| 10/09/2019 | 16:00 | Pickering College | Home | Boulden South | Exhibition Game | |
| 10/09/2019 | 16:00 | Soccer Sr Boys Div I | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 10/09/2019 | 16:00 | Soccer Jr Boys Div I | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 10/10/2019 | 10:00 | Football Sr Boys | St. Andrew's College | Home | Hargraft Field | CISAA League game |
| 10/11/2019 | 20:00 | Home | P.C.M. Rink | CISAA League game | ||
| 10/14/2019 | 16:00 | Hockey Sr Girls Div I | Home | P.C.M. Rink | ||
| 10/15/2019 | 15:00 | Field Hockey Jr Girls | Havergal College | Home | Field Hockey LS | CISAA League game |
| 10/15/2019 | 15:30 | Soccer Sr Boys Div I | Ridley College | Away | Ridley College | CISAA League game |
| 10/15/2019 | 15:30 | Ridley College | Away | Ridley College | Exhibition Game | |
| 10/15/2019 | 16:00 | Home | P.C.M. Rink | CISAA League game | ||
| 10/15/2019 | 16:15 | Field Hockey Jr Girls | Havergal College | Home | Field Hockey LS | CISAA League game |
| 10/16/2019 | 03:30 | Soccer U14 Boys Div III | Montcrest School | Home | Boulden North | CISAA League game |
| 10/16/2019 | 12:30 | Field Hockey Jr Girls | Toronto Montessori School | Away | Crosby Park | CISAA League game |
| 10/16/2019 | 14:00 | Basketball U14 Girls Div III | Ridley College | Away | Ridley College | CISAA League game |
| 10/16/2019 | 15:00 | Field Hockey Sr Girls Div I | Ridley College | Away | Ridley College | CISAA League game |
| 10/16/2019 | 15:15 | Basketball U14 Girls Div III | Bishop Strachan School | Away | Ridley College | CISAA League game |
| 10/16/2019 | 16:00 | Soccer Jr Boys Div I | Crescent School | Home | Boulden South | CISAA League game |
| 10/16/2019 | 16:00 | Field Hockey Sr Girls Div II | Villanova College | Home | Field Hockey LS | CISAA League game |
| 10/16/2019 | 19:30 | Hockey Jr Boys Div I | Roedovre- Denmark | Home | P.C.M. Rink | Exhibition Game |
| 10/17/2019 | 14:00 | Soccer U12 Boys | Montcrest School | Home | Trinity College School | Exhibition Game |
| 10/17/2019 | 14:45 | Soccer U12 Boys | Crescent School | Home | Trinity College School | Exhibition Game |
| 10/17/2019 | 15:30 | Soccer U12 Boys | Villanova College | Home | Trinity College School | Exhibition Game |
| 10/17/2019 | 15:30 | Soccer U14 Boys Div III | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 10/18/2019 | 09:00 | Soccer Sr Boys Div I | CAIS Schools | Away | St. Andrew's College | CAIS |
| 10/18/2019 | 13:00 | Harriers Sr School | To Be Announced | Away | To be confirmed | Invitational |
| 10/18/2019 | 13:30 | Hockey Sr Girls Div I | To Be Announced | Away | Queen's University | Exhibition Game |
| 10/18/2019 | 15:00 | Football Sr Boys | Upper Canada College | Away | Upper Canada College | CISAA League game |
| 10/18/2019 | 15:00 | Football Jr Boys | Norwood D.H.S. | Away | Norwood District High School | |
| 10/18/2019 | 15:00 | Basketball Jr Girls Div I | Crestwood Preparatory College | Away | Crestwood Preparatory College | CISAA League game |
| 10/18/2019 | 20:00 | Basketball Sr Girls Div I | To Be Announced | Home | Sue Burns Gym | TCS Invitational |
| 10/19/2019 | Hockey Sr Girls Div I | Home | P.C.M. Rink | Exhibition Game | ||
| 10/19/2019 | 10:00 | Basketball Sr Girls Div I | To Be Announced | Home | Sue Burns Gym | TCS Invitational |
| 10/19/2019 | 11:30 | Rosseau Lake College | Away | Rosseau Lake College | Exhibition Game | |
| 10/19/2019 | 14:00 | Hockey Jr Boys Div I | Heritage | Home | P.C.M. Rink | Exhibition Game |
| 10/19/2019 | 16:00 | Hockey Sr Boys Div I | Stanstead College | Away | Stanstead College | Exhibition Game |
| 10/20/2019 | 10:00 | Hockey Jr Boys Div I | Heritage | Home | P.C.M. Rink | Exhibition Game |
| 10/20/2019 | 12:30 | Hockey Sr Boys Div I | Stanstead College | Away | Stanstead College | Exhibition Game |
| 10/21/2019 | 16:00 | Hockey Sr Girls Div I | Home | P.C.M. Rink | ||
| 10/22/2019 | Field Hockey Sr Girls Div IB | TBA | Highest Remaining Seed | Playoff | ||
| 10/22/2019 | 15:30 | Field Hockey Sr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/22/2019 | 16:00 | Field Hockey Sr Girls Div II | St. Clement's School | Home | Field Hockey LS | CISAA League game |
| 10/23/2019 | 12:00 | Harriers Sr School | C.I.S.A.A. Schools | Home | Trinity College School | CISAA Championships |
| 10/23/2019 | 14:00 | Basketball Jr Girls Div I | St. Clement's School | Away | Branksome Hall | CISAA League game |
| 10/23/2019 | 15:00 | Soccer U14 Boys Div III | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/23/2019 | 15:30 | Field Hockey Jr Girls | C.I.S.A.A. Schools | Away | Trinity College School | Playoff |
| 10/23/2019 | 15:30 | Soccer Jr Boys Div I | De La Salle | Away | De La Salle | CISAA League game |
| 10/23/2019 | 15:30 | Field Hockey Jr Girls | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/23/2019 | 15:30 | Basketball U14 Girls Div III | Pickering College | Home | Sue Burns Gym | CISAA League game |
| 10/23/2019 | 15:30 | Basketball Jr Girls Div I | Branksome Hall | Away | Branksome Hall | CISAA League game |
| 10/23/2019 | 16:00 | Field Hockey Sr Girls Div II | Lakefield College School | Home | Field Hockey LS | CISAA League game |
| 10/24/2019 | Field Hockey Sr Girls Div IB | TBA | Highest Remaining Seed | CISAA Championship Game | ||
| 10/24/2019 | 15:30 | Field Hockey Sr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championship Game |
| 10/25/2019 | 15:00 | Football Jr Boys | North Hastings S.S. | Home | Hay Field | |
| 10/25/2019 | 20:00 | Hockey Sr Boys Div I | Blyth Academy-Georgetown | Home | P.C.M. Rink | Exhibition Game |
| 10/26/2019 | Hockey Sr Girls Div I | Home | P.C.M. Rink | Exhibition Game | ||
| 10/26/2019 | 10:00 | Field Hockey Jr Girls | C.I.S.A.A. Schools | Home | Trinity College School | CISAA Championships |
| 10/26/2019 | 10:00 | Field Hockey Sr Girls Div II | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/26/2019 | 10:00 | Field Hockey Jr Girls | C.I.S.A.A. Schools | Home | Field Hockey LS | CISAA Championships |
| 10/26/2019 | 10:00 | Soccer U14 Boys Div III | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championship Game |
| 10/26/2019 | 10:00 | Soccer U12 Boys | C.I.S.A.A. Schools | Away | Hillfield Strathallan College | Tournament |
| 10/26/2019 | 13:00 | Football Sr Boys | Huron Heights | Away | Huron Heights Sec. School | CISAA League game |
| 10/26/2019 | 13:30 | Soccer Sr Boys Div I | Upper Canada College | Home | Bigside Soccer Field | CISAA League game |
| 10/26/2019 | 13:30 | Soccer Jr Boys Div I | Upper Canada College | Home | Boulden South | CISAA League game |
| 10/28/2019 | 16:00 | Hockey Sr Girls Div I | Home | P.C.M. Rink | ||
| 10/29/2019 | 15:30 | Basketball Sr Girls Div I | Villanova College | Away | Villanova College | CISAA League game |
| 10/30/2019 | 14:00 | Field Hockey Sr Girls Div II | C.I.S.A.A. Schools | Away | Bayview Glen | CISAA Championships |
| 10/30/2019 | 15:00 | Soccer Jr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/30/2019 | 15:30 | Basketball Jr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/30/2019 | 15:30 | Soccer Sr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/30/2019 | 15:30 | Basketball U14 Girls Div III | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/31/2019 | 13:00 | Football Sr Boys | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 10/31/2019 | 15:00 | Football Jr Boys | Kawartha Schools | Away | To Be Announced | |
| 11/01/2019 | 15:00 | Soccer Sr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 11/01/2019 | 16:00 | Basketball Sr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 11/01/2019 | 18:00 | Hockey Jr Boys Div I | A21 Academy | Away | Windsor | Exhibition Game |
| 11/01/2019 | 20:00 | Hockey Sr Boys Div I | A21 Academy | Away | Windsor | Exhibition Game |
| 11/02/2019 | 08:00 | Hockey Jr Boys Div I | A21 Academy | Away | Windsor | Exhibition Game |
| 11/02/2019 | 09:00 | Hockey Sr Girls Div I | To Be Announced | Away | Buffalo, NY | Tournament |
| 11/02/2019 | 09:00 | Harriers Sr School | O.F.S.A.A. | Away | Sudbury | OFSAA Championships |
| 11/02/2019 | 09:30 | Basketball U14 Girls Div III | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championships |
| 11/02/2019 | 09:30 | Basketball Jr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championships |
| 11/02/2019 | 10:00 | Hockey Sr Boys Div I | A21 Academy | Away | Windsor | Exhibition Game |
| 11/02/2019 | 11:00 | Soccer Jr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 11/03/2019 | 09:00 | Hockey Sr Girls Div I | To Be Announced | Away | Buffalo, NY | Tournament |
| 11/05/2019 | 13:00 | Basketball Sr Girls Div I | C.I.S.A.A. Schools | Away | 1st Place in League | CISAA Championships |
| 11/05/2019 | 15:00 | Soccer Jr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championship Game |
| 11/06/2019 | 13:00 | Football Sr Boys | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championship Game |
| 11/06/2019 | 15:00 | Soccer Sr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championship Game |
| 11/08/2019 | 15:00 | Football Jr Boys | Kawartha Schools | Away | To Be Announced | |
| 11/15/2019 | 09:00 | Hockey Sr Boys Div I | To Be Announced | Home | P.C.M. Rink | |
| 11/15/2019 | 16:00 | Hockey Jr Boys Div I | Loyola High School | Away | Loyola High School | Exhibition Game |
| 11/16/2019 | 09:00 | Hockey Sr Boys Div I | To Be Announced | Home | P.C.M. Rink | |
| 11/16/2019 | 11:30 | Hockey Jr Boys Div I | Loyola High School | Away | Loyola High School | Exhibition Game |
| 11/17/2019 | 09:00 | Hockey Sr Boys Div I | To Be Announced | Home | P.C.M. Rink | |
| 11/19/2019 | 15:30 | Hockey Sr Boys Div I | Ridley College | Home | P.C.M. Rink | CISAA League game |
| 11/20/2019 | 15:00 | Hockey Jr Boys Div I | St. Michael's College | Home | P.C.M. Rink | Exhibition Game |
| 11/21/2019 | 13:30 | Upper Canada College | Away | Mayfair Lakeshore | CISAA League game | |
| 11/22/2019 | Hockey Jr Boys Div I | To Be Announced | Away | New Hampton, New Hampshire | ||
| 11/22/2019 | 09:00 | Hockey Sr Boys Div I | To Be Announced | Away | New Hampton, New Hampshire | |
| 11/23/2019 | Hockey Sr Boys Div I | To Be Announced | Away | To Be Announced | ||
| 11/23/2019 | Hockey Jr Boys Div I | To Be Announced | Away | To Be Announced | ||
| 11/23/2019 | Hockey Jr Boys Div I | To Be Announced | Away | To Be Announced | ||
| 11/24/2019 | Hockey Sr Boys Div I | To Be Announced | Away | To Be Announced | ||
| 11/24/2019 | Hockey Jr Boys Div I | To Be Announced | Away | To Be Announced | ||
| 11/26/2019 | 15:00 | Hockey Jr Boys Div I | Nichols School | Home | P.C.M. Rink | CISAA League game |
| 11/27/2019 | 15:45 | Basketball Sr Boys Div III | Holy Trinity School | Away | Holy Trinity School | CISAA League game |
| 11/27/2019 | 15:45 | Basketball Sr Boys Div III | Holy Trinity School | Home | Lower Gym | CISAA League game |
| 11/27/2019 | 16:30 | Hockey Sr Boys Div I | St. Michael's College | Home | P.C.M. Rink | CISAA League game |
| 11/29/2019 | 13:00 | Hockey Sr Girls Div I | To Be Announced | Away | Brampton | Tournament |
| 11/29/2019 | 19:00 | Hockey Sr Boys Div I | Appleby | Home | P.C.M. Rink | Exhibition Game |
| 11/30/2019 | 09:00 | Hockey Sr Girls Div I | To Be Announced | Away | Brampton | Tournament |
| 11/30/2019 | 11:00 | Basketball Sr Boys Div IB | Appleby | Away | Appleby College | CISAA League game |
| 11/30/2019 | 11:00 | Appleby | Away | Appleby College | CISAA League game | |
| 11/30/2019 | 15:00 | Hockey Sr Boys Div I | Ridley College | Away | Ridley College | CISAA League game |
| 12/01/2019 | 09:00 | Hockey Sr Girls Div I | To Be Announced | Away | Brampton | Tournament |
| 12/11/2019 | 15:00 | Hockey Sr Girls Div I | Nichols School | Home | P.C.M. Rink | CISAA League game |
| 12/11/2019 | 15:30 | Volleyball Sr Girls Div IB | Bayview Glen | Away | Bayview Glen | CISAA League game |
| 12/11/2019 | 15:45 | Basketball Sr Boys Div IB | Greenwood College School | Away | Greenwood College School | CISAA League game |
| 12/11/2019 | 16:00 | Hockey Jr Boys Div I | Upper Canada College | Away | Upper Canada College | Exhibition Game |
| 12/11/2019 | 16:00 | Basketball Sr Boys Div III | Bayview Glen | Home | Lower Gym | CISAA League game |
| 12/11/2019 | 16:30 | Hockey Sr Boys Div I | Nichols School | Home | P.C.M. Rink | CISAA League game |
| 12/11/2019 | 16:30 | Volleyball Sr Girls Div IB | St. Mildred's Lightbourne | Home | Sue Burns Gym- South | CISAA League game |
| 12/13/2019 | Hockey Sr Girls Div I | To Be Announced | Away | University of Toronto | Tournament | |
| 12/13/2019 | 16:30 | Hockey Jr Boys Div I | Lower Canada College | Away | Lower Canada College | Exhibition Game |
| 12/14/2019 | 10:00 | Hockey Jr Boys Div I | Bishop's College School | Away | Bishop's-Lennoxville | Exhibition Game |
| 12/14/2019 | 12:00 | Hockey Sr Boys Div I | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 12/17/2019 | 15:00 | Royal St. George's College | Away | Royal St. George's College | CISAA League game | |
| 12/17/2019 | 15:30 | Basketball U14 Boys Div III | St. John's Kilmarnock | Away | St. John's Kilmarnock | CISAA League game |
| 12/17/2019 | 16:00 | Basketball Sr Boys Div III | Toronto French School | Home | Lower Gym | CISAA League game |
| 12/17/2019 | 16:30 | Basketball Sr Boys Div IB | Royal St. George's College | Away | Royal St. George's College | CISAA League game |
| 01/05/2020 | 15:00 | Basketball U12 Boys | Holy Trinity School | Home | Trinity College School | CISAA League game |
| 01/05/2020 | 15:00 | Basketball U12 Boys | York School | Home | Trinity College School | CISAA League game |
| 01/05/2020 | 16:00 | Basketball U12 Boys | Crescent School | Home | Trinity College School | CISAA League game |
| 01/05/2020 | 16:00 | Basketball U12 Boys | St. Andrew's College | Home | Trinity College School | CISAA League game |
| 01/08/2020 | 15:30 | Holy Trinity School | Home | Trinity College School | CISAA League game | |
| 01/08/2020 | 15:30 | Basketball Sr Boys Div III | De La Salle | Home | Lower Gym | CISAA League game |
| 01/08/2020 | 16:00 | Hockey Sr Boys Div I | Upper Canada College | Away | Upper Canada College | CISAA League game |
| 01/10/2020 | Hockey Jr Boys Div I | To Be Announced | Home | P.C.M. Rink | TCS Invitational | |
| 01/10/2020 | 09:00 | Home | P.C.M. Rink | CISAA League game | ||
| 01/10/2020 | 09:00 | Hockey Sr Girls Div I | To Be Announced | Away | Nichols School | Tournament |
| 01/11/2020 | Hockey Jr Boys Div I | To Be Announced | Home | P.C.M. Rink | TCS Invitational | |
| 01/11/2020 | 11:00 | Volleyball Jr Girls Div II | St. John's Kilmarnock | Away | St. John's Kilmarnock | CISAA League game |
| 01/12/2020 | Hockey Jr Boys Div I | To Be Announced | Home | P.C.M. Rink | TCS Invitational | |
| 01/13/2020 | 15:00 | Volleyball U14 Girls Div III | Ridley College | Away | Crestwood Preparatory College | CISAA League game |
| 01/13/2020 | 16:00 | Volleyball U14 Girls Div III | Crestwood Preparatory College | Away | Crestwood Preparatory College | CISAA League game |
| 01/14/2020 | 16:00 | Basketball U14 Boys Div III | Toronto Montessori School | Away | Toronto Montessori School- JR | CISAA League game |
| 01/15/2020 | 15:00 | Hockey Sr Girls Div I | Appleby | Home | P.C.M. Rink | CISAA League game |
| 01/15/2020 | 16:00 | Basketball Sr Boys Div IB | Appleby | Away | Appleby College | CISAA League game |
| 01/15/2020 | 16:00 | Volleyball Jr Girls Div II | Toronto French School | Away | Toronto French School JR | CISAA League game |
| 01/15/2020 | 16:00 | Volleyball Sr Girls Div IB | Toronto French School | Away | Toronto French School JR | CISAA League game |
| 01/15/2020 | 16:00 | Hockey Sr Boys Div I | Appleby | Away | Appleby College | Exhibition Game |
| 01/15/2020 | 16:00 | Appleby | Home | Trinity College School | CISAA League game | |
| 01/15/2020 | 16:00 | Basketball Sr Boys Div IB | Appleby | Home | Sue Burns Gym | CISAA League game |
| 01/17/2020 | 20:00 | Hockey Sr Boys Div I | Bowling Green High School | Home | P.C.M. Rink | Exhibition Game |
| 01/18/2020 | 07:00 | Home | P.C.M. Rink | |||
| 01/18/2020 | 10:00 | Volleyball Sr Girls Div IB | Appleby | Away | Appleby College | CISAA League game |
| 01/18/2020 | 10:00 | Volleyball Jr Girls Div II | Lakefield College School | Away | St. Mildred's Lightbourn | CISAA League game |
| 01/18/2020 | 11:00 | Basketball Sr Boys Div III | Lakefield College School | Home | Lower Gym | CISAA League game |
| 01/18/2020 | 11:15 | Volleyball Sr Girls Div IB | Ridley College | Away | Appleby College | CISAA League game |
| 01/21/2020 | 14:30 | Basketball U12 Boys | Bayview Glen | Home | Trinity College School | CISAA League game |
| 01/21/2020 | 14:30 | Basketball U14 Boys Div III | Bayview Glen | Home | Sue Burns Gym | CISAA League game |
| 01/22/2020 | Basketball Sr Boys Div III | St. Andrew's College | Away | St. Andrew's College | CISAA League game | |
| 01/22/2020 | 15:00 | Volleyball Sr Girls Div IB | Bishop Strachan School | Home | Sue Burns Gym- South | CISAA League game |
| 01/22/2020 | 15:00 | Hockey Sr Girls Div I | Bishop Strachan School | Home | P.C.M. Rink | CISAA League game |
| 01/22/2020 | 15:45 | Hockey Sr Boys Div I | St. Michael's College | Away | St. Michael's College | CISAA League game |
| 01/22/2020 | 16:00 | Basketball Sr Boys Div IB | Royal St. George's College | Home | Sue Burns Gym | CISAA League game |
| 01/22/2020 | 16:00 | Royal St. George's College | Home | Trinity College School | CISAA League game | |
| 01/22/2020 | 17:00 | Volleyball Sr Girls Div IB | Lakefield College School | Home | Sue Burns Gym- South | CISAA League game |
| 01/24/2020 | 16:00 | Hockey Jr Boys Div I | Ulysse Academy | Away | Montreal | Tournament |
| 01/25/2020 | Hockey Jr Boys Div I | Ulysse Academy | Away | Montreal | Tournament | |
| 01/25/2020 | 11:00 | Hockey Sr Girls Div I | Ridley College | Home | P.C.M. Rink | CISAA League game |
| 01/25/2020 | 12:00 | Volleyball U14 Girls Div III | Greenwood College School | Home | Upper Gym | CISAA League game |
| 01/25/2020 | 13:00 | Volleyball U14 Girls Div III | St. John's Kilmarnock | Away | St. John's Kilmarnock | CISAA League game |
| 01/26/2020 | Hockey Jr Boys Div I | Ulysse Academy | Away | Montreal | Tournament | |
| 01/29/2020 | Hockey Jr Boys Div I | St. Andrew's College | TBA | To Be Announced | Exhibition Game | |
| 01/29/2020 | 14:30 | Volleyball U14 Girls Div III | Toronto Montessori School | Away | Toronto Montessori School- JR | CISAA League game |
| 01/29/2020 | 14:30 | Toronto Montessori School | Away | Toronto Montessori School- JR | CISAA League game | |
| 01/29/2020 | 15:00 | Basketball U14 Boys Div III | Crestwood Preparatory College | Away | Crestwood Preparatory College | CISAA League game |
| 01/29/2020 | 15:00 | Hockey Sr Girls Div I | Havergal College | Home | P.C.M. Rink | CISAA League game |
| 01/29/2020 | 15:30 | Holy Trinity School | Home | Trinity College School | CISAA League game | |
| 01/29/2020 | 15:30 | Volleyball U14 Girls Div III | Montcrest School | Away | Toronto Montessori School- JR | CISAA League game |
| 01/29/2020 | 15:30 | St. John's Kilmarnock | Away | Toronto Montessori School- JR | CISAA League game | |
| 01/29/2020 | 15:30 | Volleyball Jr Girls Div II | Greenwood College School | Home | Sue Burns Gym | CISAA League game |
| 01/29/2020 | 16:00 | Basketball Sr Boys Div IB | Greenwood College School | Home | Sue Burns Gym | CISAA League game |
| 01/29/2020 | 16:30 | Volleyball Jr Girls Div II | Havergal College | Home | Sue Burns Gym | CISAA League game |
| 01/31/2020 | 15:00 | Hockey Jr Boys Div I | Nichols School | Away | Nichols School | Exhibition Game |
| 01/31/2020 | 18:00 | Hockey Sr Girls Div I | Nichols School | Away | Nichols School | CISAA League game |
| 01/31/2020 | 19:30 | Hockey Sr Boys Div I | Nichols School | Away | Nichols School | CISAA League game |
| 02/01/2020 | Hockey Sr Boys Div I | Shady Side Academy | Away | Pittsburgh PA | Exhibition Game | |
| 02/01/2020 | Hockey Jr Boys Div I | Nichols School | Away | Nichols School | Exhibition Game | |
| 02/01/2020 | Hockey Sr Girls Div I | Shady Side Academy | Away | Pittsburgh PA | Exhibition Game | |
| 02/02/2020 | Hockey Sr Girls Div I | Shady Side Academy | Away | Pittsburgh PA | Exhibition Game | |
| 02/02/2020 | Hockey Sr Boys Div I | Shady Side Academy | Away | Pittsburgh PA | Exhibition Game | |
| 02/05/2020 | 14:30 | Volleyball Sr Girls Div IB | De La Salle | Home | Sue Burns Gym- South | CISAA League game |
| 02/05/2020 | 15:00 | Rosseau Lake College | Away | Trafalgar Castle School | CISAA League game | |
| 02/05/2020 | 15:30 | Basketball U14 Boys Div III | Montcrest School | Home | Sue Burns Gym | CISAA League game |
| 02/05/2020 | 15:30 | Basketball U12 Boys | Montcrest School | Home | Trinity College School | CISAA League game |
| 02/05/2020 | 16:00 | Hockey Jr Boys Div I | St. Michael's College | Away | St. Michael's College | Exhibition Game |
| 02/05/2020 | 16:00 | Basketball Sr Boys Div IB | Appleby | Away | Appleby College | CISAA League game |
| 02/05/2020 | 16:00 | Hockey Sr Girls Div I | Appleby | Away | Appleby College | CISAA League game |
| 02/05/2020 | 16:00 | Appleby | Away | Appleby College | CISAA League game | |
| 02/05/2020 | 16:00 | Trafalgar Castle School | Away | Trafalgar Castle School | CISAA League game | |
| 02/05/2020 | 16:00 | Basketball Sr Boys Div III | St. Andrew's College | Home | Lower Gym | CISAA League game |
| 02/05/2020 | 16:30 | Volleyball Sr Girls Div IB | St. Clement's School | Home | Sue Burns Gym- South | CISAA League game |
| 02/07/2020 | Hockey Jr Boys Div I | Somang Hockey | Away | Montreal | Exhibition Game | |
| 02/07/2020 | 08:00 | Hockey Sr Boys Div I | To Be Announced | Home | P.C.M. Rink | |
| 02/08/2020 | Hockey Jr Boys Div I | Somang Hockey | Away | Montreal | Exhibition Game | |
| 02/08/2020 | 08:00 | Hockey Sr Boys Div I | To Be Announced | Home | P.C.M. Rink | |
| 02/09/2020 | Hockey Jr Boys Div I | Somang Hockey | Away | Montreal | Exhibition Game | |
| 02/09/2020 | 08:00 | Hockey Sr Boys Div I | To Be Announced | Home | P.C.M. Rink | |
| 02/10/2020 | 15:00 | Hockey Jr Boys Div I | Upper Canada College | Home | P.C.M. Rink | Exhibition Game |
| 02/12/2020 | 14:30 | Volleyball U14 Girls Div III | Pickering College | Home | Upper Gym | CISAA League game |
| 02/12/2020 | 14:30 | Volleyball Jr Girls Div II | St. Clement's School | Home | Sue Burns Gym | CISAA League game |
| 02/12/2020 | 15:00 | Hockey Sr Girls Div I | Bishop Strachan School | Away | Rinx Arena | CISAA League game |
| 02/12/2020 | 15:00 | Holy Name of Mary CS | Home | Trinity College School | CISAA League game | |
| 02/12/2020 | 15:30 | Volleyball Jr Girls Div II | Bishop Strachan School | Home | Sue Burns Gym | CISAA League game |
| 02/12/2020 | 15:30 | Basketball Sr Boys Div IB | Greenwood College School | Home | Sue Burns Gym | CISAA League game |
| 02/12/2020 | 15:30 | Basketball U14 Boys Div III | Greenwood College School | Home | Sue Burns Gym | CISAA League game |
| 02/12/2020 | 15:45 | Holy Trinity School | Away | Holy Trinity School | CISAA League game | |
| 02/12/2020 | 16:00 | Basketball Sr Boys Div III | Crescent School | Away | Crescent School | CISAA League game |
| 02/12/2020 | 16:00 | Volleyball Sr Girls Div IB | Pickering College | Away | Pickering College | CISAA League game |
| 02/12/2020 | 16:00 | Hockey Jr Boys Div I | Nichols School | Away | Nichols School | Exhibition Game |
| 02/12/2020 | 16:30 | Volleyball U14 Girls Div III | Trafalgar Castle School | Home | Upper Gym | CISAA League game |
| 02/12/2020 | 16:30 | Hockey Sr Boys Div I | St. Andrew's College | Home | P.C.M. Rink | CISAA League game |
| 02/12/2020 | 17:00 | Albert College | Home | Trinity College School | CISAA League game | |
| 02/19/2020 | 14:30 | Hockey Sr Girls Div I | Havergal College | Away | Rinx Arena | CISAA League game |
| 02/19/2020 | 15:00 | Volleyball Jr Girls Div II | Appleby | Home | Sue Burns Gym | CISAA League game |
| 02/19/2020 | 15:30 | Basketball U14 Boys Div III | Pickering College | Away | Pickering College | CISAA League game |
| 02/19/2020 | 16:00 | Basketball Sr Boys Div III | Country Day School | Home | Lower Gym | CISAA League game |
| 02/19/2020 | 16:30 | Basketball Sr Boys Div IB | Royal St. George's College | Away | Royal St. George's College | CISAA League game |
| 02/19/2020 | 16:30 | Royal St. George's College | Away | Royal St. George's College | CISAA League game | |
| 02/19/2020 | 16:30 | Hockey Sr Boys Div I | Upper Canada College | Home | P.C.M. Rink | CISAA League game |
| 02/19/2020 | 17:00 | Volleyball Jr Girls Div II | Lakefield College School | Home | Sue Burns Gym | CISAA League game |
| 02/21/2020 | 19:30 | Hockey Jr Boys Div I | Loyola High School | Home | P.C.M. Rink | Exhibition Game |
| 02/22/2020 | Volleyball U14 Girls Div III | TBA | 1st Place in League | Playoff | ||
| 02/22/2020 | Basketball U12 Boys | TBA | Host to be confirmed | CISAA Championship Game | ||
| 02/22/2020 | 11:00 | Hockey Jr Boys Div I | Loyola High School | Home | P.C.M. Rink | Exhibition Game |
| 02/24/2020 | Volleyball Sr Girls Div IB | TBA | 1st Place in League | Playoff | ||
| 02/24/2020 | Basketball Sr Boys Div III | TBA | 1st Place in League | Playoff | ||
| 02/24/2020 | Volleyball U14 Girls Div III | TBA | 1st Place in League | Playoff | ||
| 02/24/2020 | Basketball U14 Boys Div III | TBA | 1st Place in League | Playoff | ||
| 02/24/2020 | Volleyball Jr Girls Div II | TBA | 1st Place in League | Playoff | ||
| 02/24/2020 | TBA | 1st Place in League | Playoff | |||
| 02/26/2020 | Basketball Sr Boys Div III | TBA | 1st Place in League | Playoff | ||
| 02/26/2020 | Volleyball U14 Girls Div III | TBA | 1st Place in League | CISAA Championship Game | ||
| 02/26/2020 | Basketball U14 Boys Div III | TBA | 1st Place in League | Playoff | ||
| 02/26/2020 | Volleyball Jr Girls Div II | TBA | 1st Place in League | Playoff | ||
| 02/26/2020 | Squash Sr Boys | TBA | Mayfair Lakeshore | CISAA Championship Game | ||
| 02/26/2020 | TBA | 1st Place in League | Playoff | |||
| 02/26/2020 | TBA | 1st Place in League | Playoff | |||
| 02/26/2020 | Basketball Sr Boys Div IB | TBA | Highest Remaining Seed | Playoff | ||
| 02/26/2020 | Volleyball Sr Girls Div IB | TBA | 1st Place in League | Playoff | ||
| 02/26/2020 | 15:00 | Hockey Sr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 02/28/2020 | Volleyball Sr Girls Div IB | TBA | 1st Place in League | CISAA Championship Game | ||
| 02/28/2020 | Volleyball Jr Girls Div II | TBA | 1st Place in League | CISAA Championship Game | ||
| 02/28/2020 | Hockey Sr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff | |
| 02/28/2020 | TBA | 1st Place in League | CISAA Championship Game | |||
| 02/28/2020 | 15:00 | Hockey Sr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff |
| 02/29/2020 | Hockey Jr Boys Div I | Northwood School- New York | Away | Northwood - Lake Placid | Exhibition Game | |
| 02/29/2020 | TBA | 1st Place in League | CISAA Championship Game | |||
| 02/29/2020 | Hockey Sr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | Playoff | |
| 02/29/2020 | Basketball Sr Boys Div IB | TBA | Highest Remaining Seed | CISAA Championship Game | ||
| 02/29/2020 | Basketball Sr Boys Div III | TBA | 1st Place in League | CISAA Championship Game | ||
| 02/29/2020 | Basketball U14 Boys Div III | TBA | 1st Place in League | CISAA Championship Game | ||
| 03/01/2020 | Hockey Jr Boys Div I | Northwood School- New York | Away | Northwood - Lake Placid | Exhibition Game | |
| 03/01/2020 | Hockey Sr Boys Div I | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championships | |
| 03/03/2020 | 15:00 | Hockey Sr Girls Div I | C.I.S.A.A. Schools | Away | To Be Announced | CISAA Championship Game |
| 03/05/2020 | Hockey Sr Boys Div I | To Be Announced | Away | St. Andrew's College | ||
| 03/06/2020 | Hockey Sr Boys Div I | To Be Announced | Away | St. Andrew's College | ||
| 03/07/2020 | Hockey Sr Boys Div I | To Be Announced | Away | St. Andrew's College | ||
| 04/15/2020 | 14:30 | Badminton Sr Coed | Crestwood Preparatory College | Home | Sue Burns Gym | CISAA League game |
| 04/15/2020 | 14:30 | Badminton Jr Coed | Crestwood Preparatory College | Home | West Gym | CISAA League game |
| 04/22/2020 | : | Badminton Sr Coed | Bayview Glen | Away | Bayview Glen | CISAA League game |
| 04/22/2020 | : | Havergal-Crescent | Away | Havergal College | CISAA League game | |
| 04/22/2020 | : | Havergal-Crescent | Away | Havergal College | CISAA League game | |
| 04/22/2020 | : | Havergal-Crescent | Away | Havergal College | CISAA League game | |
| 04/22/2020 | : | Tennis Sr Boys | Lakefield College School | Away | Lakefield College School | CISAA League game |
| 04/22/2020 | : | Soccer Sr Girls Spring Div I | Ridley College | Away | Ridley College | CISAA League game |
| 04/22/2020 | 03:30 | Tennis Sr Girls | Lakefield College School | Home | Massey '55 Tennis Center | CISAA League game |
| 04/22/2020 | 15:30 | Badminton Jr Coed | Bayview Glen | Away | Bayview Glen | CISAA League game |
| 04/23/2020 | 15:00 | Havergal-Crescent | Away | Havergal College | CISAA League game | |
| 04/25/2020 | 22:00 | Badminton Jr Coed | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 04/25/2020 | 22:00 | Badminton Sr Coed | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 04/27/2020 | 16:00 | BishopSS-St.Mike's | Home | Trinity College School | CISAA League game | |
| 04/29/2020 | 03:30 | Soccer U14 Girls Spring Div II | Montcrest School | Home | Boulden North | CISAA League game |
| 04/29/2020 | 15:00 | Badminton Sr Coed | York School | Home | Sue Burns Gym | CISAA League game |
| 04/29/2020 | 15:00 | Greenwood College School | Away | Cherry Beach Park | CISAA League game | |
| 04/29/2020 | 15:00 | Tennis Sr Girls | Bayview Glen | Home | Massey '55 Tennis Center | CISAA League game |
| 04/29/2020 | 15:30 | Soccer Sr Girls Spring Div I | De La Salle | Away | De La Salle | CISAA League game |
| 04/29/2020 | 16:00 | De La Salle | Home | Trinity College School | CISAA League game | |
| 04/29/2020 | 16:00 | Badminton Jr Coed | Royal St. George's College | Home | West Gym | CISAA League game |
| 04/29/2020 | 16:00 | Badminton Sr Coed | Royal St. George's College | Home | Sue Burns Gym | CISAA League game |
| 05/02/2020 | Tennis Sr Girls | Greenwood College School | Away | Greenwood College School | CISAA League game | |
| 05/02/2020 | 10:30 | Tennis Sr Boys | Greenwood College School | Home | Massey '55 Tennis Center | CISAA League game |
| 05/02/2020 | 22:00 | Badminton Sr Coed | Appleby | Home | Sue Burns Gym | CISAA League game |
| 05/05/2020 | 16:00 | Rugby Sr Boys Div I | Crescent School | Home | Hay Field | CISAA League game |
| 05/05/2020 | 16:00 | Rugby Jr Boys Div I | Crescent School | Home | Hargraft Field | CISAA League game |
| 05/05/2020 | 22:30 | Albert College | Home | Trinity College School | CISAA League game | |
| 05/06/2020 | Soccer Sr Girls Spring Div II | Trafalgar Castle School | Away | Trafalgar Castle School | CISAA League game | |
| 05/06/2020 | : | BishopSS-St.Mike's | Away | Bishop Strachan School | CISAA League game | |
| 05/06/2020 | 15:00 | Baseball Sr Boys | St. Michael's College | Away | St. Michael's College | CISAA League game |
| 05/06/2020 | 15:00 | Badminton Sr Coed | Upper Canada College | Home | Sue Burns Gym | CISAA League game |
| 05/06/2020 | 15:30 | Badminton Sr Coed | Trafalgar Castle School | Away | Trafalgar Castle School | CISAA League game |
| 05/06/2020 | 15:30 | Trafalgar Castle School | Away | Trafalgar Castle School | CISAA League game | |
| 05/06/2020 | 15:30 | Badminton Jr Coed | Upper Canada College | Home | West Gym | CISAA League game |
| 05/06/2020 | 16:00 | Soccer Sr Girls Spring Div I | Appleby | Away | Appleby College | CISAA League game |
| 05/09/2020 | 22:30 | Rugby Jr Boys Div I | Appleby | Home | Hargraft Field | CISAA League game |
| 05/09/2020 | 22:30 | Rugby Sr Boys Div I | Appleby | Home | Hay Field | CISAA League game |
| 05/09/2020 | 23:00 | Badminton Jr Coed | Ridley College | Away | Ridley College | CISAA League game |
| 05/09/2020 | 23:00 | Badminton Sr Coed | Ridley College | Away | Ridley College | CISAA League game |
| 05/11/2020 | : | Tennis Sr Girls | Bishop Strachan School | Away | Mayfair East | CISAA League game |
| 05/11/2020 | 16:00 | Tennis Sr Boys | Royal St. George's College | Home | Massey '55 Tennis Center | CISAA League game |
| 05/13/2020 | Rugby Jr Boys Div I | Upper Canada College | Away | Upper Canada College | CISAA League game | |
| 05/13/2020 | Baseball Sr Boys | Upper Canada College | Away | Upper Canada College | CISAA League game | |
| 05/13/2020 | Rugby Sr Boys Div I | Upper Canada College | Away | Upper Canada College | CISAA League game | |
| 05/13/2020 | 12:30 | Tennis Sr Boys | Toronto French School | Away | Toronto French School JR | CISAA League game |
| 05/13/2020 | 15:00 | Soccer Sr Girls Spring Div I | Bishop Strachan School | Home | Boulden South | CISAA League game |
| 05/13/2020 | 15:30 | Soccer U14 Girls Spring Div II | Trafalgar Castle School | Home | Boulden North | CISAA League game |
| 05/13/2020 | 15:30 | Badminton Jr Coed | Trafalgar Castle School | Home | West Gym | CISAA League game |
| 05/13/2020 | 15:30 | Badminton Sr Coed | Greenwood College School | Away | Greenwood College School | CISAA League game |
| 05/13/2020 | 16:00 | De La Salle | Home | Trinity College School | CISAA League game | |
| 05/20/2020 | Soccer Sr Girls Spring Div I | TBA | Highest Remaining Seed | Playoff | ||
| 05/20/2020 | Badminton Sr Coed | TBA | Trinity College School | CISAA Championship Game | ||
| 05/20/2020 | Badminton Jr Coed | TBA | Crescent School | CISAA Championship Game | ||
| 05/20/2020 | Tennis Sr Girls | TBA | Mayfair East | CISAA Championship Game | ||
| 05/20/2020 | Tennis Sr Boys | TBA | Mayfair West | CISAA Championship Game | ||
| 05/20/2020 | Baseball Sr Boys | TBA | Host to be confirmed | CISAA Championship Game | ||
| 05/20/2020 | Soccer Sr Girls Spring Div II | TBA | 1st Place in League | Playoff | ||
| 05/20/2020 | Soccer U14 Girls Spring Div II | TBA | East 1st Place | Playoff | ||
| 05/20/2020 | 16:00 | Rugby Sr Boys Div I | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 05/20/2020 | 16:00 | Rugby Jr Boys Div I | St. Andrew's College | Away | St. Andrew's College | CISAA League game |
| 05/22/2020 | TBA | 1st Place in League | CISAA Championship Game | |||
| 05/23/2020 | Rugby Jr Boys Div I | TBA | 1st Place in League | CISAA Championship Game | ||
| 05/23/2020 | Soccer Sr Girls Spring Div II | TBA | 1st Place in League | CISAA Championship Game | ||
| 05/23/2020 | TBA | 1st Place in League | CISAA Championship Game | |||
| 05/23/2020 | Soccer U14 Girls Spring Div II | TBA | East 1st Place | CISAA Championship Game | ||
| 05/23/2020 | Soccer Sr Girls Spring Div I | TBA | Highest Remaining Seed | CISAA Championship Game | ||
| 05/23/2020 | Rugby Sr Boys Div I | TBA | 1st Place in League | CISAA Championship Game |