Round: 25 Ground: Hardcourt outdoor
| Wimbledon - Qual. | 2016/06/22 12:15 | Tim Smyczek v Hiroki Moriya | 1-6,6-3,4-6 |
| Wimbledon - Qual. | 2016/06/20 18:05 | Tim Smyczek v Ilya Ivashka | 7-6,6-2 |
| Open di Francia - Qual. | 2016/05/16 15:25 | Tim Smyczek v Adrian Ungur | 2-6,7-6,3-6 |
| Challenger Bordeaux | 2016/05/09 15:00 | Tim Smyczek v Quentin Halys | 2-6,3-6 |
| Challenger Tallahassee | 2016/04/26 16:10 | Tim Smyczek v Brian Baker | 4-6,5-7 |
| Challenger Savannah | 2016/04/20 00:00 | Tim Smyczek v Frances Tiafoe | 4-6,2-6 |
| Challenger Sarasota | 2016/04/12 21:00 | Frances Tiafoe v Tim Smyczek | 6-4,6-3 |
| ATP Houston | 2016/04/08 18:35 | Tim Smyczek v Feliciano Lopez | 2-6,3-6 |
| 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 Canada F1 - Qual. | 2016/02/28 15:00 | Kevin Kylar v Ivan Mitric | 6-3,6-1 |