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