Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2014/09/02 14:00 | Philip Bester v Max Wennakoski | 6-3,6-4 |
| ITF Canada F8 | 2014/08/23 18:00 | Philip Bester v Blake Mott | 7-6,6-7,3-6 |
| ITF Canada F8 | 2014/08/22 17:00 | Philip Bester v Greg Jones | 3-6,6-3,6-2 |
| ITF Canada F7 | 2014/08/15 23:45 | Omar Jasika v Philip Bester | 4-6,7-6,6-4 |
| ITF Canada F4 | 2014/07/05 22:15 | Filip Peliwo v Philip Bester | 6-4,6-4 |
| ITF Canada F4 | 2014/07/04 17:00 | Philip Bester v Mousheg Hovhannisyan | 7-6,6-2 |
| ITF Canada F4 | 2014/07/03 17:00 | Philip Bester v Collin Johns | 6-3,6-2 |
| ITF Canada F4 | 2014/07/02 17:00 | Philip Bester v Jayson Amos | 7-6,6-3 |
| ITF Canada F9 Qual | 2014/09/02 21:00 | Egor Koleganov v Maksim Tikhomirov | 6-4,6-2 |