Round: 25 Ground: Hardcourt outdoor
| ITF USA F16 | 2016/05/05 14:50 | Philip Bester v Victor Krustev | 6-3,6-2 |
| ITF Canada F2 | 2015/03/11 22:00 | Philip Bester v Victor Krustev | 6-1,6-2 |
| ITF Canada F4 | 2016/07/01 19:25 | Philip Bester v Sebastien Boltz | 6-7,4-6 |
| ITF Canada F4 | 2016/06/30 17:00 | Philip Bester v Joshua Peck | 6-3,6-2 |
| 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 Canada F4 | 2016/06/29 00:00 | Alexios Halebian v Victor Krustev | 6-2,6-0 |
| ITF Canada F3 | 2016/06/21 19:35 | Alexander Day v Victor Krustev | 6-4,6-3 |
| ITF Canada F3 Qual | 2016/06/19 17:00 | Mesa Mei v Victor Krustev | 6-3,5-7,3-6 |
| ITF Canada F3 Qual | 2016/06/18 17:00 | Gabriel Sanchez v Victor Krustev | 2-6,0-6 |
| ITF USA F19 Qual | 2016/06/12 16:00 | Victor Krustev v Max Wennakoski | 5-7,0-6 |
| ITF USA F19 Qual | 2016/06/11 15:30 | Victor Krustev v Herbert Jody Maginley | 5-7,6-2,6-3 |
| ITF USA F16 | 2016/05/05 14:50 | Philip Bester v Victor Krustev | 6-3,6-2 |
| ITF USA F16 | 2016/05/02 13:30 | Robert Levine v Victor Krustev | 6-2,4-6,1-6 |