Stadium: Court South 3 Round: 44 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2023/08/14 16:00 | Aidan Mayo v Harper, Cleeve | 6-2,6-3 |
| Challenger Winnipeg | 2023/08/13 18:05 | Harper, Cleeve v Boulais, Justin | 4-6,6-3,6-2 |
| ITF M15 South Bend | 2023/06/21 18:40 | Harper, Cleeve v Blaise Bicknell | 3-6,4-6 |
| Challenger Calgary | 2022/11/10 02:15 | Harper, Cleeve v Dominik Koepfer | 4-6,1-6 |
| Challenger Calgary | 2022/11/07 22:20 | Harper, Cleeve v Max Hans Rehberg | 7-6,3-6,6-4 |
| Vancouver, Canada | 2022/08/14 17:00 | Ulises Blanch v Harper, Cleeve | 6-2,7-6 |
| ITF M25 Champaign | 2022/07/20 20:45 | Peter Bertran v Harper, Cleeve | 4-6,6-1,6-1 |
| ITF M15 Pittsburgh | 2022/07/13 14:00 | Bernard, John v Harper, Cleeve | 7-5,7-5 |
| UTR Pro Fort Worth | 2023/09/09 14:30 | Jirousek, Tomas v Jerry Barton | 6-4,6-2 |
| UTR Pro Fort Worth | 2023/09/08 22:15 | Jirousek, Tomas v Adam Lynch | 3-6,6-1,6-4 |
| UTR Pro Fort Worth | 2023/09/06 21:00 | Jirousek, Tomas v Chad Miller | 1-6,6-1,6-2 |
| UTR Pro Fort Worth | 2023/09/06 00:42 | Jirousek, Tomas v Francesco Cordova | 6-1,5-3 |
| UTR Pro Fort Worth | 2023/09/04 22:30 | Jirousek, Tomas v Sebastian Gorzny | 6-7,3-6 |
| UTR Pro Fort Worth | 2023/09/03 22:45 | Jirousek, Tomas v Liam Krall | 6-4,6-4 |
| ITF M25 Poznan | 2023/08/23 13:30 | Alex M Pujolras v Jirousek, Tomas | 6-4,6-7,7-5 |
| ITF M25 Poznan | 2023/08/22 10:45 | Jirousek, Tomas v Lech Gontar | 6-3,6-2 |