| 27 May 1916 | | Trinity College School Lower Flat v Trinity College School Upper Flat | Trinity College School, Port Hope | Results |
| 02 Jun 1916 | | Lakefield College School Preparatory v Trinity College School Juniors | The Grove, Lakefield | Results |
| 07 Jun 1916 | | Appleby School v Trinity College School | Varsity Lawn, Toronto | Results |
| 07 Jun 1916 | | Trinity College School v Upper Canada College | Trinity College School, Port Hope | Results |
| 09 Jun 1916 | | Ridley College v Trinity College School | Rosedale, Toronto | Results |
| 10 Jun 1916 | | St Andrew's College v Trinity College School | St Andrew's College, Toronto | Results |
| 11 Jun 1916 | | Trinity College School Juniors v St Andrew's College Preparatory School | Trinity College School, Port Hope | Results |
| 14 Jun 1916 | | Trinity College School Juniors v Lakefield College School Preparatory | Trinity College School, Port Hope | Results |
| 20 May 1916 | | Lake Lodge School v Ridley College Third XI | Grimsby | Results |
| 24 May 1916 | | Ridley College v Rosedale | Ridley College, St Catharines | Results |
| 31 May 1916 | | 123rd Battalion v Ridley College Second XI | Queen Victoria Park, Niagara Falls | Results |
| 31 May 1916 | | Ridley College v 180th Battalion (Sportsmen) | Ridley College, St Catharines | Results |
| 31 May 1916 | | Ridley College Third XI v Lake Lodge School | Ridley College, St Catharines | Results |
| 20 May 1916 | | Hamilton v Ridley College | Highfield School, Hamilton | Results |
| 01 Jun 1916 | | Ridley College Second XI v 123rd Battalion | Ridley College, St Catharines | Results |
| 02 Jun 1916 | | Ridley College v St Andrew's College | Ridley College, St Catharines | Results |
| 03 Jun 1916 | | Appleby College v Ridley College Dean's House | Appleby School Ground, Oakville | Results |
| 10 Jun 1916 | | St Andrew's College Second XI v Ridley College Second XI | St Andrew's College, Toronto | Results |
| 10 Jun 1916 | | Upper Canada College v Ridley College | Upper Canada College Lord's Ground, Toronto | Results |
| 17 Jun 1916 | | Ridley College v 123rd Battalion | Ridley College, St Catharines | Results |
| 03 Jun 1916 | | Upper Canada College v St Andrew's College | Upper Canada College Lord's Ground, Toronto | Results |
| 12 Aug 1916 | | Vancouver v Victoria | High Park, Toronto | Results |
| 16 Sep 1916 | | Church and Mercantile Cricket League v Toronto City Cricket League | Varsity Lawn, Toronto | Results |
| 17 May 1916 | | Spencer's XI v J Minn's XI | Upper Brockton Oval, Vancouver | Results |
| 15 Jul 1916 | | Westmount v West Indian | Amateur Athletic Association Ground, Montreal | Results |
| 13 May 1916 | | Dovercourt v St Edmund's | Dovercourt Park, Toronto | Results |
| 02 Sep 1916 | | Five Cs v Albion Club of Vancouver | Jubilee Hospital Ground, Victoria | Results |
| 09 Sep 1916 | | The Garrison v Five Cs | Garrison Ground, Halifax | Results |
| 13 May 1916 | | Highfield School v 120th City of Hamilton Battalion | Hamilton Amateur Athletic Association Ground, Hamilton | Results |
| 13 May 1916 | | St Matthias v Mimico Old Country Club | Trinity University, Toronto | Results |
| 01 Jul 1916 | | AJ Chandler's XI v Napier's XI | Exhibition Ground, Regina | Results |
| 02 Sep 1916 | | Saskatchewan Co-Operative Elevator Company v Regina Cricket League | Exhibition Ground, Regina | Results |
| 13 May 1916 | | 195th Battalion v St Paul's | Mounted Police Barracks, Regina | Results |
| 24 May 1916 | | Albion Club of Toronto v Old Country Club | Trinity University, Toronto | Results |
| 24 May 1916 | | St Edmund's v Woodgreen Brotherhood | Dovercourt Park, Toronto | Results |
| 03 Jun 1916 | | Albion Club of Toronto v 180th Battalion (Sportsmen) | Toronto | Results |
| 03 Jun 1916 | | Woodgreen Brotherhood v Toronto City Cricket League | Riverdale Park, Toronto | Results |
| 24 Jun 1916 | | Albion Club of Toronto v St Edmund's | Trinity University, Toronto | Results |
| 01 Jul 1916 | | Woodgreen Brotherhood v St Edmund's | Riverdale Park, Toronto | Results |
| 05 Jul 1916 | | W Paris' Toronto XI v Ridley College | Rosedale, Toronto | Results |
| 08 Jul 1916 | | Albion Club of Toronto v St Matthias | Toronto | Results |
| 22 Jul 1916 | | Brantford v Old Country Club | Indian Institute Ground, Brantford | Results |
| 05 Aug 1916 | | Brantford v St George's Club of Hamilton | Ontario School for the Blind, Brantford | Results |
| 07 Aug 1916 | | Albion Club of Toronto v Island Aquatic | Toronto | Results |
| 12 Aug 1916 | | Dovercourt v St Cyprian's | Dovercourt Park, Toronto | Results |
| 19 Aug 1916 | | Birch Cliff v Evangelia | Birch Cliff | Results |
| 26 Aug 1916 | | Old Country Club v Birch Cliff | Willowvale Park, Toronto | Results |
| 04 Sep 1916 | | Church and Mercantile Cricket League v Toronto City Cricket League | Rosedale, Toronto | Results |
| 09 Sep 1916 | | Woodgreen Brotherhood v Dovercourt | Riverdale Park, Toronto | Results |
| 03 Jul 1916 | | London Asylum v Ridley College | London Asylum Cricket Club Ground, London | Results |
| 24 May 1916 | | Brantford v 125th Battalion | Ontario School for the Blind, Brantford | Results |
| 27 May 1916 | | Brantford v 125th Battalion Paris Section | Ontario School for the Blind, Brantford | Results |
| 03 Jun 1916 | | Brantford v 125th Battalion | Ontario School for the Blind, Brantford | Results |
| 10 Jun 1916 | | Brantford v 215th Battalion | Ontario School for the Blind, Brantford | Results |
| 17 Jun 1916 | | Brantford v 125th Battalion | Ontario School for the Blind, Brantford | Results |
| 24 Jun 1916 | | Brantford v 215th Battalion | Ontario School for the Blind, Brantford | Results |
| 01 Jul 1916 | | Brantford v Toronto Bantams | Ontario School for the Blind, Brantford | Results |
| 29 Jul 1916 | | St George's Club of Hamilton v Brantford | Hamilton | Results |
| 19 Aug 1916 | | Hamilton v Brantford | Hamilton | Results |
| 26 Aug 1916 | | Brantford v St George's Club of Hamilton | Ontario School for the Blind, Brantford | Results |
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