Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2014/09/09 15:55 | Daniel Nguyen v Harry Bourchier | 6-4,4-6,3-6 |
| ITF Canada F9 Qual | 2014/09/03 17:35 | Harry Bourchier v Michael Bois | 4-6,3-6 |
| ITF Canada F9 Qual | 2014/09/01 15:00 | Harry Bourchier v David Volfson | 6-1,7-6 |
| ITF Canada F9 Qual | 2014/09/10 17:35 | Cameron Silverman v Philip Bester | 3-6,3-6 |
| ITF Canada F9 Qual | 2014/09/09 18:35 | Rogelio Siller v Philip Bester | 3-6,2-6 |
| ITF Canada F9 Qual | 2014/09/04 14:00 | Philip Bester v Daniel Nguyen | 6-2,6-7,3-6 |
| ITF Canada F9 Qual | 2014/09/03 16:20 | Philip Bester v Egor Koleganov | 6-3,6-4 |
| 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 |