Stadium: Stadium 1 Round: 19 Ground: Hardcourt outdoor
| Challenger Salinas | 2023/07/26 16:20 | Beibit Zhukayev v Philip Sekulic | 7-6,6-3 |
| Challenger Salinas | 2023/07/25 19:15 | Philip Sekulic v Alexander Cozbinov | 7-6,6-4 |
| Challenger Granby | 2023/07/23 20:20 | Philip Sekulic v Alexis Galarneau | 4-6,6-3,3-6 |
| Challenger Granby | 2023/07/22 19:00 | James Trotter v Philip Sekulic | 4-6,6-2,6-7 |
| Challenger Granby | 2023/07/21 17:00 | Justin Boulais v Philip Sekulic | 3-6,2-6 |
| Challenger Granby | 2023/07/20 19:35 | Philip Sekulic v Denis Kudla | 7-5,6-3 |
| Challenger Granby | 2023/07/18 14:00 | Philip Sekulic v Yasutaka Uchiyama | 6-7,7-6,6-1 |
| Challenger Granby | 2023/07/17 17:05 | Colin Sinclair v Philip Sekulic | 3-6,4-6 |
| Challenger Lexington | 2023/07/30 15:05 | Justin Roberts v Ramkumar Ramanathan | 7-6,7-6 |
| ITF M15 Rochester | 2023/07/21 18:50 | Ignacio Monzon v Justin Roberts | 6-4,6-2 |
| ITF M15 Rochester | 2023/07/20 15:25 | Yannik Rahman v Justin Roberts | 1-6,2-6 |
| ITF M15 Rochester | 2023/07/19 14:30 | Maksim Tikhomirov v Justin Roberts | 1-6,4-6 |
| ITF M25 Laval | 2023/07/11 14:15 | Preston Brown v Justin Roberts | 6-3,7-6 |
| ITF M15 South Bend | 2023/06/21 15:00 | Justin Roberts v Axel Nefve | 1-6,1-6 |
| ITF M15 San Diego | 2023/06/08 18:35 | Justin Roberts v Jack Anthrop | 3-6,4-6 |
| ITF M15 San Diego | 2023/06/07 15:50 | Ishaan Ravichander v Justin Roberts | 2-6,6-7 |