Stadium: Court 2 Round: 19 Ground: Hardcourt outdoor
| Challenger Chicago | 2023/07/09 21:00 | Omar Jasika v Quinn Vandecasteele | 7-5,6-1 |
| Challenger Bloomfield Hills | 2023/07/07 15:00 | Omar Jasika v Tristan Schoolkate | 4-6,3-6 |
| Challenger Bloomfield Hills | 2023/07/06 16:35 | Omar Jasika v Yuta Shimizu | 6-3,6-3 |
| Challenger Bloomfield Hills | 2023/07/05 14:00 | Dane Sweeny v Omar Jasika | 5-7,1-6 |
| Challenger Bloomfield Hills | 2023/07/04 16:50 | Omar Jasika v Justin Boulais | 6-3,7-5 |
| Challenger Bloomfield Hills | 2023/07/03 20:00 | Omar Jasika v Andrew Fenty | 6-3,6-4 |
| ITF M15 Jakarta | 2023/06/23 02:00 | Omar Jasika v Cihan Akay | 6-1,6-0 |
| ITF M15 Jakarta | 2023/06/22 03:55 | Omar Jasika v Seungmin Park | 6-0,7-5 |
| 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 Palmas del Mar | 2023/06/11 18:40 | Henrik Wiersholm v Colin Sinclair | 2-6,1-6 |