Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2014/09/09 15:55 | Nguyen, Daniel v Bourchier, Harry | 6-4,4-6,3-6 |
| ITF Canada F9 Qual | 2014/09/03 17:35 | Bourchier, Harry v Bois, Michael | 4-6,3-6 |
| ITF Canada F9 Qual | 2014/09/01 15:00 | Bourchier, Harry v Volfson, David | 6-1,7-6 |
| ITF Canada F9 Qual | 2014/09/10 17:35 | Silverman, Cameron v Bester, Philip | 3-6,3-6 |
| ITF Canada F9 Qual | 2014/09/09 18:35 | Siller, Rogelio v Bester, Philip | 3-6,2-6 |
| ITF Canada F9 Qual | 2014/09/04 14:00 | Bester, Philip v Nguyen, Daniel | 6-2,6-7,3-6 |
| ITF Canada F9 Qual | 2014/09/03 16:20 | Bester, Philip v Koleganov, Egor | 6-3,6-4 |
| ITF Canada F9 Qual | 2014/09/02 14:00 | Bester, Philip v Wennakoski, Max | 6-3,6-4 |
| ITF Canada F8 | 2014/08/23 18:00 | Bester, Philip v Blake Mott | 7-6,6-7,3-6 |
| ITF Canada F8 | 2014/08/22 17:00 | Bester, Philip v Jones, Greg | 3-6,6-3,6-2 |
| Canada F7, Singles | 2014/08/15 23:45 | Omar Jasika v Bester, Philip | 4-6,7-6,6-4 |