Round: 25 Ground: Hardcourt outdoor
| Wimbledon Qual | 2016/06/22 12:15 | Smyczek, Tim v Hiroki Moriya | 1-6,6-3,4-6 |
| Wimbledon Qual | 2016/06/20 18:05 | Smyczek, Tim v Ilya Ivashka | 7-6,6-2 |
| French Open Qual | 2016/05/16 15:25 | Smyczek, Tim v Ungur, Adrian | 2-6,7-6,3-6 |
| Challenger - Bordeaux | 2016/05/09 15:00 | Smyczek, Tim v Quentin Halys | 2-6,3-6 |
| Challenger - Tallahassee | 2016/04/26 16:10 | Smyczek, Tim v Baker, Brian | 4-6,5-7 |
| Challenger - Savannah | 2016/04/20 00:00 | Smyczek, Tim v Frances Tiafoe | 4-6,2-6 |
| Challenger - Sarasota | 2016/04/12 21:00 | Frances Tiafoe v Smyczek, Tim | 6-4,6-3 |
| ATP - Houston | 2016/04/08 18:35 | Smyczek, Tim v Lopez, Feliciano | 2-6,3-6 |
| ITF Canada F5 | 2016/07/07 20:00 | Halebian, Alexios v Kylar, Kevin | 6-4,6-1 |
| ITF Canada F4 | 2016/06/29 18:35 | Bester, Philip v Kylar, Kevin | 6-1,6-3 |
| ITF Canada F3 | 2016/06/22 18:35 | Kylar, Kevin v Bester, Philip | 2-6,1-6 |
| ITF Bulgaria F1 | 2016/05/18 09:30 | Prudnikau, Aliaksandr v Kylar, Kevin | 6-3,6-1 |
| ITF USA F12 Qual | 2016/04/04 14:00 | Denis Shapovalov v Kylar, Kevin | 6-2,6-0 |
| ITF USA F10 Qual | 2016/03/12 21:00 | Evan Zhu v Kylar, Kevin | 6-1,4-6,6-3 |
| ITF Canada F1 Qual | 2016/02/29 15:00 | Kylar, Kevin v Lin, Jack Mingjie | 4-6,1-6 |
| ITF Canada F1 Qual | 2016/02/28 15:00 | Kylar, Kevin v Mitric, Ivan | 6-3,6-1 |