Stadium: Cancha N. Lapenti Round: 25 Ground: Hardcourt outdoor
| Challenger Granby | 2023/07/18 01:00 | Alexis Galarneau v Omar Jasika | 6-1,3-6,6-3 |
| Challenger Chicago | 2023/07/11 15:00 | Mark Lajal v Omar Jasika | 6-1,6-4 |
| Challenger Chicago | 2023/07/10 17:05 | Omar Jasika v Colin Sinclair | 6-4,6-4 |
| 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 Granby | 2023/07/19 20:40 | Maxime Janvier v Adam Walton | 6-4,4-6,7-6 |
| Challenger Granby | 2023/07/18 23:30 | Adam Walton v Vasek Pospisil | 6-7,7-6,6-1 |
| Challenger Chicago | 2023/07/13 20:20 | Adam Walton v Giovanni Mpetshi Perricard | 6-7,4-6 |
| Challenger Chicago | 2023/07/10 22:00 | Eliot Spizzirri v Adam Walton | 2-6,2-6 |
| Challenger Bloomfield Hills | 2023/07/04 20:50 | Kei Nishikori v Adam Walton | 6-1,6-2 |
| ITF M25 Tulsa | 2023/06/25 14:00 | Adam Walton v Nick Chappell | 6-1,6-3 |
| ITF M25 Tulsa | 2023/06/24 13:55 | Adam Walton v Aidan Mchugh | 6-1,6-3 |
| ITF M25 Tulsa | 2023/06/23 13:55 | Adam Walton v Ethan Quinn | 6-2,7-6 |