Stadium: Stadium Court Round: 1
| International Tennis Series | 2020/05/28 12:00 | John Bernard v Oskar Michalek | 2-4,4-3,4-1 |
| International Tennis Series | 2020/05/26 17:15 | Oskar Michalek v Ronald Hohmann | 4-3,4-0 |
| International Tennis Series | 2020/05/26 15:00 | Oskar Michalek v Henry Barrett | 4-0,4-1 |
| International Tennis Series | 2020/05/26 13:00 | Jakub Wojcik v Oskar Michalek | 4-3,4-1 |
| International Tennis Series | 2020/05/22 00:15 | Kyle Seelig v Oskar Michalek | 4-2,4-2 |
| International Tennis Series | 2020/05/21 22:15 | Oskar Michalek v Dmitry Popko | 2-4,4-1,1-4 |
| International Tennis Series | 2020/05/21 21:20 | Tyler Mercier v Oskar Michalek | 4-0,4-3 |
| International Tennis Series | 2020/05/07 16:45 | Oskar Michalek v Stefan Storch | 4-2,3-4,3-4 |
| International Tennis Series | 2020/05/26 19:15 | Cleeve Harper v Liam Draxl | 4-3,1-4,2-4 |
| International Tennis Series | 2020/05/26 14:25 | Jamie Cerretani v Cleeve Harper | 1-4,4-3,1-4 |
| International Tennis Series | 2020/05/23 16:30 | Cleeve Harper v Adam El Mihdawy | 3-4,1-4 |
| Challenger Calgary | 2020/02/25 17:00 | Matias Franco Descotte v Cleeve Harper | 6-7,7-6,6-4 |
| ITF M15 Austin | 2019/11/21 16:00 | Harrison Adams v Cleeve Harper | 6-2,6-2 |
| ITF M15 Austin | 2019/11/19 17:30 | Cleeve Harper v Eliot Spizzirri | 6-4,6-4 |
| ITF M15 Pittsburgh | 2019/07/04 16:15 | Cleeve Harper v Paul Oosterbaan | 3-6,3-6 |
| ITF M15 Pittsburgh | 2019/07/02 14:00 | Michal Wozniak v Cleeve Harper | 2-6,4-6 |