Round: 44 Ground: Clay
| ITF Canada F2 | 2014/03/12 15:00 | Edward Corrie v Dean O'Brien | 5-7,6-4,6-3 |
| ITF Canada F1 | 2014/03/06 15:00 | Richard Gabb v Dean O'Brien | 5-7,6-4,6-3 |
| ITF Canada F1 | 2014/03/05 18:10 | Adam El Mihdawy v Dean O'Brien | 4-6,4-6 |
| Challenger Morelos | 2014/02/17 16:00 | Dennis Novikov v Dean O'Brien | 5-7,6-4,1-6 |
| ITF Canada F2 | 2014/03/11 15:40 | Riaan Du Toit v Pavel Krainik | 3-6,4-6 |
| ITF Canada F1 | 2014/03/06 22:05 | Pavel Krainik v Germain Gigounon | 3-6,4-6 |