| CRE21 | Tue | May 21 | 21:00 | Crosby Park Richmond Hill | Richmond Hill Raiders Green U21 | Cherry Beach U21 |
| CRE21 | Thu | May 23 | 21:00 | William Bond Park | Oak Ridges Knights | Pickering FC U21 |
| CRE21 | Fri | May 24 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | Aurora FC U21 |
| CRE21 | Sun | May 26 | 19:00 | Eastgate #2 | Peterborough City U21 | East York U21CRE |
| CRE21 | Mon | May 27 | 21:00 | Fleury Park | Aurora FC U21 | Cherry Beach U21 |
| CRE21 | Tue | May 28 | 20:45 | Dieppe Park | East York U21CRE | NYFC Strikers U21 |
| CRE21 | Tue | May 28 | 21:00 | Crosby Park Richmond Hill | Richmond Hill Raiders Green U21 | Oak Ridges Knights |
| CRE21 | Thu | May 30 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | Richmond Hill Raiders Green U21 |
| CRE21 | Thu | May 30 | 21:00 | William Bond Park | Oak Ridges Knights | Peterborough City U21 |
| CRE21 | Sun | Jun 2 | 19:00 | Eastgate #2 | Peterborough City U21 | Cherry Beach U21 |
| CRE21 | Tue | Jun 4 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | NYFC Strikers U21 |
| CRE21 | Tue | Jun 4 | 21:00 | Richmond Green East | Richmond Hill Raiders Green U21 | Aurora FC U21 |
| CRE21 | Wed | Jun 5 | 20:45 | Dieppe Park | East York U21CRE | Cherry Beach U21 |
| CRE21 | Thu | Jun 6 | 21:00 | Eastgate #2 | Peterborough City U21 | Pickering FC U21 |
| CRE21 | Fri | Jun 7 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | Oak Ridges Knights |
| CRE21 | Mon | Jun 10 | 21:00 | Fleury Park | Aurora FC U21 | Pickering FC U21 |
| CRE21 | Tue | Jun 11 | 21:00 | Richmond Green East | Richmond Hill Raiders Green U21 | Peterborough City U21 |
| CRE21 | Wed | Jun 12 | 20:45 | Dieppe Park | East York U21CRE | Oak Ridges Knights |
| CRE21 | Thu | Jun 13 | 21:00 | Eastgate #2 | Peterborough City U21 | Aurora FC U21 |
| CRE21 | Fri | Jun 14 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | Cherry Beach U21 |
| CRE21 | Mon | Jun 17 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | Pickering FC U21 |
| CRE21 | Mon | Jun 17 | 21:00 | Fleury Park | Aurora FC U21 | Peterborough City U21 |
| CRE21 | Tue | Jun 18 | 21:00 | Dieppe Park | East York U21CRE | Richmond Hill Raiders Green U21 |
| CRE21 | Thu | Jun 20 | 21:00 | William Bond Park | Oak Ridges Knights | Cherry Beach U21 |
| CRE21 | Thu | Jun 20 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | East York U21CRE |
| CRE21 | Fri | Jun 21 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | Richmond Hill Raiders Green U21 |
| CRE21 | Mon | Jun 24 | 21:00 | Fleury Park | Aurora FC U21 | Oak Ridges Knights |
| CRE21 | Tue | Jun 25 | 21:00 | Crosby Park Richmond Hill | Richmond Hill Raiders Green U21 | East York U21CRE |
| CRE21 | Thu | Jun 27 | 21:00 | TBD #3 | Cherry Beach U21 | Pickering FC U21 |
| CRE21 | Fri | Jun 28 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | Peterborough City U21 |
| CRE21 | Tue | Jul 2 | 21:00 | Fleury Park | Aurora FC U21 | NYFC Strikers U21 |
| CRE21 | Thu | Jul 4 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | Oak Ridges Knights |
| CRE21 | Thu | Jul 4 | 21:00 | Dieppe Park | East York U21CRE | Peterborough City U21 |
| CRE21 | Thu | Jul 4 | 21:00 | TBD #3 | Cherry Beach U21 | Richmond Hill Raiders Green U21 |
| CRE21 | Sun | Jul 7 | 19:00 | Eastgate #2 | Peterborough City U21 | NYFC Strikers U21 |
| CRE21 | Mon | Jul 8 | 21:00 | Fleury Park | Aurora FC U21 | East York U21CRE |
| CRE21 | Thu | Jul 11 | 21:00 | TBD #3 | Cherry Beach U21 | Peterborough City U21 |
| CRE21 | Thu | Jul 11 | 21:00 | William Bond Park | Oak Ridges Knights | Richmond Hill Raiders Green U21 |
| CRE21 | Thu | Jul 11 | 21:00 | Dieppe Park | East York U21CRE | Aurora FC U21 |
| CRE21 | Sun | Jul 14 | 19:00 | William Bond Park | Oak Ridges Knights | Aurora FC U21 |
| CRE21 | Thu | Jul 18 | 21:00 | TBD #3 | Cherry Beach U21 | Aurora FC U21 |
| CRE21 | Thu | Jul 18 | 21:00 | Eastgate #2 | Peterborough City U21 | Oak Ridges Knights |
| CRE21 | Fri | Jul 19 | 19:00 | Downsview Turf 1 | NYFC Strikers U21 | East York U21CRE |
| CRE21 | Sun | Jul 21 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | Cherry Beach U21 |
| CRE21 | Mon | Jul 22 | 21:00 | Fleury Park | Aurora FC U21 | Richmond Hill Raiders Green U21 |
| CRE21 | Thu | Jul 25 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | Peterborough City U21 |
| CRE21 | Thu | Jul 25 | 21:00 | TBD #3 | Cherry Beach U21 | East York U21CRE |
| CRE21 | Thu | Jul 25 | 21:00 | William Bond Park | Oak Ridges Knights | NYFC Strikers U21 |
| CRE21 | Sun | Jul 28 | 19:00 | Eastgate #2 | Peterborough City U21 | Richmond Hill Raiders Green U21 |
| CRE21 | Tue | Jul 30 | 21:00 | Crosby Park Richmond Hill | Richmond Hill Raiders Green U21 | Pickering FC U21 |
| CRE21 | Thu | Aug 1 | 21:00 | Kinsmen Park 2 | Pickering FC U21 | Aurora FC U21 |
| CRE21 | Thu | Aug 1 | 21:00 | William Bond Park | Oak Ridges Knights | East York U21CRE |
| CRE21 | Thu | Aug 1 | 21:00 | TBD #3 | Cherry Beach U21 | NYFC Strikers U21 |
| CRE21 | Tue | Aug 6 | 21:00 | Richmond Green East | Richmond Hill Raiders Green U21 | NYFC Strikers U21 |
| CRE21 | Wed | Aug 7 | 20:45 | Dieppe Park | East York U21CRE | Pickering FC U21 |
| CRE21 | Thu | Aug 8 | 21:00 | TBD #3 | Cherry Beach U21 | Oak Ridges Knights |