Stadium: Stadium Round: 25 Ground: Grass
| ATP Washington | 2018/08/01 17:25 | Tim Smyczek v Mischa Zverev | 2-6,6-7 |
| ATP Atlanta | 2018/07/24 20:50 | Tim Smyczek v Mischa Zverev | 3-6,7-6,3-6 |
| Wimbledon | 2019/07/01 11:25 | Steve Darcis v Mischa Zverev | 6-2,6-4,6-4 |
| ATP Halle | 2019/06/16 11:10 | Andreas Seppi v Mischa Zverev | 6-3,6-2 |
| ATP Halle | 2019/06/15 11:45 | Mischa Zverev v Lloyd Harris | 6-3,5-7,6-4 |
| ATP Stuttgart | 2019/06/10 09:00 | Mischa Zverev v Jo-Wilfried Tsonga | 3-6,0-6 |
| French Open | 2019/05/27 10:40 | Mischa Zverev v Richard Gasquet | 3-6,4-6,3-6 |
| ATP Geneva | 2019/05/19 15:45 | Mischa Zverev v Juan Ignacio Londero | 4-6,4-6 |
| ATP Madrid | 2019/05/04 17:00 | Mischa Zverev v Reilly Opelka | 6-7,6-7 |
| ATP Munich | 2019/04/30 12:45 | Guido Pella v Mischa Zverev | 6-2,6-1 |
| ATP Newport | 2019/07/15 15:00 | John-Patrick Smith v Tim Smyczek | 4-6,6-3,2-6 |
| ATP Newport | 2019/07/14 17:00 | Tim Smyczek v Mitchell Krueger | 6-3,6-1 |
| Challenger Winnetka | 2019/07/09 00:00 | Jared Hiltzik v Tim Smyczek | 6-2,3-6,6-3 |
| Wimbledon | 2019/06/26 11:25 | Corentin Moutet v Tim Smyczek | 6-1,6-3 |
| Wimbledon | 2019/06/24 10:00 | Mitchell Krueger v Tim Smyczek | 5-7,4-6 |
| Challenger Columbus | 2019/06/13 18:00 | Mikael Torpegaard v Tim Smyczek | 6-2,6-1 |
| Challenger Columbus | 2019/06/12 14:00 | Zsombor Piros v Tim Smyczek | 3-6,6-4,2-6 |
| Challenger Little Rock | 2019/06/07 19:05 | Tim Smyczek v Christopher Eubanks | 6-7,3-6 |