| 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 F1 Qual | 2016/02/29 15:00 | Kevin Kylar v Jack Mingjie Lin | 4-6,1-6 |
| ITF USA F23 Qual | 2016/06/26 14:30 | Michael Riechmann v Jason Legall | 6-4,4-6,5-7 |
| ITF USA F23 Qual | 2016/06/25 15:30 | Michael Riechmann v Roy Smith | 3-6,6-4,7-5 |
| ITF USA F21 Qual | 2016/06/18 17:30 | Dane Webb v Michael Riechmann | 6-3,7-5 |
| ITF USA F30 | 2015/10/12 16:35 | Michael Riechmann v Pedro Scocuglia | 6-4,6-7,0-6 |
| ITF USA F19 Qual | 2015/06/22 18:45 | Michael Riechmann v Henry Craig | 0-6,1-6 |
| ITF USA F17 | 2015/06/17 18:55 | Hans Hach Verdugo v Michael Riechmann | 7-5,7-5 |
| ITF USA F17 Qual | 2015/06/16 14:00 | Michael Riechmann v Antoine Leduc | 6-7,6-1,6-4 |
| ITF USA F23 | 2014/08/06 14:00 | Michael Riechmann v Bjorn Fratangelo | 3-6,4-6 |