Round: 26 Ground: Hardcourt outdoor
| ITF Canada F4 | 2016/06/29 18:35 | Philip Bester v Kevin Kylar | 6-1,6-3 |
| ITF Canada F3 | 2016/06/24 18:00 | Peter Polansky v Philip Bester | 4-6,6-3,6-2 |
| ITF Canada F3 | 2016/06/23 17:00 | Michael Genender v Philip Bester | 1-6,0-6 |
| ITF Canada F3 | 2016/06/22 18:35 | Kevin Kylar v Philip Bester | 2-6,1-6 |
| ITF USA F17 | 2016/06/08 15:50 | Philip Bester v Dominic Cotrone | 6-3,3-6,6-3 |
| ITF USA F16 | 2016/05/07 14:00 | Roberto Quiroz v Philip Bester | 6-2,6-4 |
| ITF USA F16 | 2016/05/06 14:00 | Philip Bester v Miomir Kecmanovic | 7-5,6-3 |
| ITF USA F16 | 2016/05/05 18:00 | Philip Bester v Matias Franco Descotte | 7-6,6-3 |
| ITF Canada F4 | 2016/06/29 20:00 | Jarryd Chaplin v Joshua Peck | 6-7,6-7 |
| ITF Canada F3 | 2016/06/22 18:10 | Finn Tearney v Joshua Peck | 4-6,7-6,6-1 |
| Challenger Drummondville Qual | 2016/03/12 20:05 | Victor Krustev v Joshua Peck | 6-4,3-6,6-3 |
| ITF Canada F2 | 2016/03/09 16:30 | Joshua Peck v Hugo Nys | 3-6,2-6 |
| ITF Canada F2 | 2016/03/08 18:25 | Joshua Peck v Nicaise Muamba | 6-4,7-6 |
| ITF Canada F2 Qual | 2016/03/07 17:05 | Mico Santiago v Joshua Peck | 7-5,6-4 |
| ITF Canada F2 Qual | 2016/03/06 13:00 | Iancu-Iustinian Ghinda v Joshua Peck | 3-6,4-6 |
| ITF Canada F1 Qual | 2016/02/28 15:00 | Jack Mingjie Lin v Joshua Peck | 4-6,7-6,6-4 |