| ITF Canada F6 | 2016/08/30 16:00 | Rubin Statham v Kevin Kylar | 6-3,6-1 |
| Challenger Winnipeg | 2016/07/11 15:00 | Tim Smyczek v Kevin Kylar | 6-1,6-1 |
| ITF Canada F5 | 2016/07/07 20:00 | Alexios Halebian v Kevin Kylar | 6-4,6-1 |
| ITF Canada F4 | 2016/06/29 18:35 | Philip Bester v Kevin Kylar | 6-1,6-3 |
| ITF Canada F3 | 2016/06/22 18:35 | Kevin Kylar v Philip Bester | 2-6,1-6 |
| ITF Bulgaria F1 | 2016/05/18 09:30 | Aliaksandr Prudnikau v Kevin Kylar | 6-3,6-1 |
| ITF USA F12 Qual | 2016/04/04 14:00 | Denis Shapovalov v Kevin Kylar | 6-2,6-0 |
| ITF USA F10 Qual | 2016/03/12 21:00 | Evan Zhu v Kevin Kylar | 6-1,4-6,6-3 |
| ITF Canada F9 Qual | 2016/09/21 15:50 | Lev Kazakov v Ivan Endara | 6-7,6-3,6-2 |
| ITF Canada F8 | 2016/09/14 16:05 | Benjamin Sigouin v Ivan Endara | 6-4,6-2 |
| ITF Canada F8 | 2016/09/13 19:05 | Juan Carlos Aguilar v Ivan Endara | 2-6,4-6 |
| ITF Canada F7 | 2016/09/11 15:30 | Frank Dancevic v Ivan Endara | 7-6,7-6 |
| ITF Canada F7 | 2016/09/10 16:30 | Alexander Ritschard v Ivan Endara | 7-6,4-6,3-6 |
| ITF Canada F7 | 2016/09/09 16:00 | Ivan Endara v David Volfson | 6-3,2-6,6-1 |
| ITF Canada F7 | 2016/09/08 16:00 | Ivan Endara v Manuel Sanchez | 4-6,6-4,6-2 |
| ITF Canada F7 | 2016/09/06 19:00 | Takanyi Garanganga v Ivan Endara | 6-2,2-6,1-6 |