Stadium: Center Court Round: 27 Ground: Hardcourt outdoor
| Challenger Charleston | 2023/09/28 14:00 | Oliver Crawford v Laurent Lokoli | 7-6,6-2 |
| Challenger Charleston | 2023/09/27 15:35 | Tennys Sandgren v Oliver Crawford | 5-7,2-6 |
| ITF M25 Kigali | 2023/09/17 09:30 | Oliver Crawford v Corentin Denolly | 6-1,4-6,4-6 |
| ITF M25 Kigali | 2023/09/16 09:30 | Oliver Crawford v Guy Orly Iradukunda | 6-1,6-0 |
| ITF M25 Kigali | 2023/09/15 09:40 | Oliver Crawford v Vadym Ursu | 6-2,6-2 |
| ITF M25 Kigali | 2023/09/14 08:40 | Oliver Crawford v Abraham Asaba | 6-4,6-1 |
| ITF M25 Kigali | 2023/09/13 09:45 | Oliver Crawford v Raghav Jaisinghani | 6-2,6-1 |
| ITF M25 Kigali | 2023/09/10 08:55 | Oliver Crawford v Damien Wenger | 4-6,2-6 |
| Challenger Charleston | 2023/09/28 15:55 | Strong Kirchheimer v Stefan Dostanic | 6-7,3-6 |
| Challenger Charleston | 2023/09/26 13:30 | Stefan Dostanic v Alexander Ritschard | 6-4,6-4 |
| Challenger Charleston | 2023/09/25 17:05 | Stefan Dostanic v Stefan Kozlov | 6-2,6-1 |
| Challenger Charleston | 2023/09/25 14:00 | Evan Zhu v Stefan Dostanic | 6-4,5-7,0-6 |
| Challenger - Cary | 2023/08/09 20:40 | Nicolas Moreno De Alboran v Stefan Dostanic | 6-2,7-6 |
| Challenger - Cary | 2023/08/08 20:15 | Stefan Dostanic v Zachary Svajda | 7-6,6-3 |
| Challenger - Cary | 2023/08/07 16:00 | Stefan Dostanic v Yuki Mochizuki | 3-6,6-3,6-1 |
| Challenger - Cary | 2023/08/06 16:30 | Philip Sekulic v Stefan Dostanic | 5-7,6-4,1-6 |