Stadium: Court 1 Round: 14 Ground: Hardcourt outdoor
| Challenger Chicago | 2023/07/10 17:05 | Omar Jasika v Colin Sinclair | 6-4,6-4 |
| Challenger Chicago | 2023/07/09 19:05 | Strong Kirchheimer v Colin Sinclair | 6-7,4-6 |
| Challenger Bloomfield Hills | 2023/07/03 20:50 | Evan Zhu v Colin Sinclair | 7-5,1-6,6-2 |
| Challenger Bloomfield Hills | 2023/07/03 14:15 | Patrick Maloney v Colin Sinclair | 7-6,6-7,3-6 |
| ITF M25 Tulsa | 2023/06/20 16:00 | Adam Neff v Colin Sinclair | 4-6,7-5,7-5 |
| Challenger Palmas del Mar | 2023/06/14 15:00 | Liam Draxl v Colin Sinclair | 7-6,6-3 |
| Challenger Palmas del Mar | 2023/06/13 20:00 | Colin Sinclair v Alexander Bravo | 6-2,6-0 |
| Challenger Palmas del Mar | 2023/06/12 15:00 | Kaito Uesugi v Colin Sinclair | 1-6,6-7 |
| Challenger Chicago | 2023/07/10 15:00 | Ernesto Escobedo v Martin Damm | 7-6,6-1 |
| Challenger Chicago | 2023/07/09 15:00 | Martin Damm v Alex Bolt | 7-6,6-4 |
| ITF M25 Santo Domingo | 2023/07/02 13:30 | Martin Damm v Liam Draxl | 7-6,6-4 |
| ITF M25 Santo Domingo | 2023/06/30 13:30 | Martin Damm v Tauheed Browning | 6-4,6-3 |
| ITF M25 Santo Domingo | 2023/06/29 15:45 | Martin Damm v Enmanuel Munoz | 6-3,6-2 |
| ITF M25 Santo Domingo | 2023/06/27 15:30 | Martin Damm v Daniel Antonio Nunez | 6-3,7-6 |
| Challenger Prostejov | 2023/06/04 11:00 | Martin Damm v Illya Marchenko | 4-6,3-6 |
| ITF M25 Jablonec Nad Nisou | 2023/06/01 09:00 | Martin Damm v Evgeny Karlovskiy | 6-3,6-2 |