| 29 Apr 1944 | | Defence v Christ Church Cathedral | Rideau Hall, Ottawa | Results |
| 29 Apr 1944 | | Ottawa v New Edinburgh | Ashbury College, Ottawa | Results |
| 06 May 1944 | | Ashbury College v Christ Church Cathedral | Ashbury College, Ottawa | Results |
| 06 May 1944 | | Ottawa v Defence | Rideau Hall, Ottawa | Results |
| 11 May 1944 | | Defence and New Edinburgh v Royal Australian Air Force | Ashbury College, Ottawa | Results |
| 11 May 1944 | | Ottawa v Ashbury College | Rideau Hall, Ottawa | Results |
| 13 May 1944 | | Lower Canada College v Wanderers | Lower Canada College, Montreal | Results |
| 20 May 1944 | | Ashbury College v Defence | Ashbury College, Ottawa | Results |
| 20 May 1944 | | Bishop's College School, Lennoxville v Lower Canada College | Bishop's College, Lennoxville | Results |
| 20 May 1944 | | Christ Church Cathedral v New Edinburgh | Rideau Hall, Ottawa | Results |
| 27 May 1944 | | New Edinburgh v Ashbury College | Rideau Hall, Ottawa | Results |
| 02 Jun 1944 | | Ashbury College v Lower Canada College | Ashbury College, Ottawa | Results |
| 03 Jun 1944 | | Bishop's College School, Lennoxville v Ashbury College | Lower Canada College, Montreal | Results |
| 03 Jun 1944 | | Bishop's College School, Lennoxville Juniors v Selwyn House School | Percival Molson Stadium, Montreal | Results |
| 23 Jun 1944 | | Victoria Rifles v Black Watch | Lower Canada College, Montreal | Results |
| 09 Sep 1944 | | Christ Church Cathedral v Ottawa Valley Cricket Council | Rideau Hall, Ottawa | Results |
| 16 Sep 1944 | | Christ Church Cathedral and Ottawa v Defence and New Edinburgh | Rideau Hall, Ottawa | Results |
| 23 Sep 1944 | | New Edinburgh and Ottawa v Christ Church Cathedral and Defence | Rideau Hall, Ottawa | Results |
| 13 May 1944 | | Ridley College v Mount Hope Royal Canadian Air Force Station | Ridley College, St Catharines | Results |
| 17 May 1944 | | Ridley College v Mount Hope Royal Canadian Air Force Station | Ridley College, St Catharines | Results |
| 20 May 1944 | | Ridley College v Mount Hope Royal Canadian Air Force Station | Ridley College, St Catharines | Results |
| 22 May 1944 | | Ridley College v Toronto Cricket Club | Ridley College, St Catharines | Results |
| 27 May 1944 | | Ridley College v St Andrew's College | Ridley College, St Catharines | Results |
| 03 Jun 1944 | | Ridley College v Trinity College School | Armour Heights, Toronto | Results |
| 31 May 1944 | | St Andrew's College v Trinity College School | St Andrew's College, Aurora | Results |
| 03 Jun 1944 | | St Andrew's College v Upper Canada College | St Andrew's College, Aurora | Results |
| 29 Apr 1944 | | Trinity College School v Peterborough | Trinity College School, Port Hope | Results |
| 01 May 1944 | | Trinity College School v Trinity College School Masters | Trinity College School, Port Hope | Results |
| 24 May 1944 | | Trinity College School v Mountain View Royal Canadian Air Force | Trinity College School, Port Hope | Results |
| 24 May 1944 | | Trinity College School v Picton Royal Canadian Air Force | Trinity College School, Port Hope | Results |
| 27 May 1944 | | Trinity College School v Kingston Royal Canadian Air Force Station | Trinity College School, Port Hope | Results |
| 07 Jun 1944 | | Trinity College School v Upper Canada College | Trinity College School, Port Hope | Results |
| 15 Jun 1944 | | Trinity College School v Picton Royal Canadian Air Force | Trinity College School, Port Hope | Results |
| 31 May 1944 | | Upper Canada College v Ridley College | Upper Canada College Lord's Ground, Toronto | Results |
| 01 Jul 1944 | | Ottawa Valley Cricket Council v Australian XI | Rideau Hall, Ottawa | Results |
| 05 Aug 1944 | | Defence v Ottawa | Rideau Hall, Ottawa | Results |
| 04 Sep 1944 | | Ottawa v Defence | Ashbury College, Ottawa | Results |
| 22 Jul 1944 | | No 31 Royal Air Force DeWinton v No 34 Royal Air Force Medicine Hat | Riley Park, Calgary | Results |
| 23 Jul 1944 | | No 2 Wireless Training School v No 34 Royal Air Force Medicine Hat | Riley Park, Calgary | Results |
| 02 Sep 1944 | | St John's Zingari v No 34 Royal Air Force Medicine Hat | Riley Park, Calgary | Results |
| 03 Sep 1944 | | No 31 Royal Air Force DeWinton v No 34 Royal Air Force Medicine Hat | Riley Park, Calgary | Results |
| 04 Sep 1944 | | Calgary v No 34 Royal Air Force Medicine Hat | Riley Park, Calgary | Results |
| 05 Aug 1944 | | No 3 Macleod v No 7 Macleod | Riley Park, Calgary | Results |
| 27 May 1944 | | Royal York-Riverdale v Mount Hope Royal Canadian Air Force Station | Toronto | Results |
| 01 Jul 1944 | | Eglinton v St Simon's Church | Toronto | Results |
| 01 Jul 1944 | | Royal York-Riverdale v Royal Air Force Jarvis | Dentonia Park, Toronto | Results |
| 05 Aug 1944 | | West Toronto v Royal Australian Air Force | High Park, Toronto | Results |
| 19 Aug 1944 | | Toronto and District Cricket Council v Royal Air Force | Armour Heights, Toronto | Results |
| 20 Aug 1944 | | Toronto v Royal Air Force | Armour Heights, Toronto | Results |
| 26 Aug 1944 | | Peterborough v Picton Royal Canadian Air Force | The Oval, Peterborough | Results |
| 09 Sep 1944 | | Picton Royal Canadian Air Force v Peterborough | Agricultural Grounds, Picton | Results |
| 20 May 1944 | | Ridley College Second XI v Upper Canada College Second XI | Ridley College, St Catharines | Results |
| 31 May 1944 | | Upper Canada College Second XI v Ridley College Second XI | Upper Canada College Lord's Ground, Toronto | Results |
| 07 Jun 1944 | | Appleby School v Ridley College Second XI | Appleby School Ground, Oakville | Results |
| 01 Jul 1944 | | Toronto v Kingston Royal Canadian Air Force Station | Armour Heights, Toronto | Results |
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