| ITF Canada F2 | 03/12 15:00 | - | Edward Corrie v Dean O'Brien | 5-7,6-4,6-3 | |
| ITF Canada F1 | 03/06 15:00 | - | Richard Gabb v Dean O'Brien | 5-7,6-4,6-3 | |
| ITF Canada F1 | 03/05 18:10 | - | Adam El Mihdawy v Dean O'Brien | 4-6,4-6 | |
| Challenger Morelos | 02/17 16:00 | 44 | Dennis Novikov v Dean O'Brien | 5-7,6-4,1-6 |