Stadium: Court 1 Round: 2
| Challenger Granby | 2023/07/17 17:05 | Colin Sinclair v Philip Sekulic | 3-6,4-6 |
| Challenger Granby | 2023/07/16 22:30 | Colin Sinclair v Martin Damm | 6-7,7-6,6-3 |
| 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 | 2023/07/02 18:00 | 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 |