Stadium: Court 15 Round: 25 Ground: Hardcourt outdoor
| Challenger Lexington | 2023/08/03 18:20 | Aidan Mayo v Tristan Schoolkate | 3-6,6-4,6-3 |
| Challenger Lexington | 2023/08/01 17:05 | Philip Sekulic v Tristan Schoolkate | 6-3,6-7,1-6 |
| Challenger Salinas | 2023/07/25 16:50 | Tristan Schoolkate v Matija Pecotic | 5-7,6-7 |
| Challenger Granby | 2023/07/21 23:20 | Alexis Galarneau v Tristan Schoolkate | 6-4,6-3 |
| Challenger Granby | 2023/07/19 15:50 | Tristan Schoolkate v Arthur Cazaux | 6-3,6-3 |
| Challenger Granby | 2023/07/18 16:25 | Tristan Schoolkate v Joshua Sheehy | 6-2,6-3 |
| Challenger Chicago | 2023/07/13 18:20 | Tristan Schoolkate v Ethan Quinn | 6-4,3-6,2-6 |
| Challenger Chicago | 2023/07/11 15:00 | Altug Celikbilek v Tristan Schoolkate | 4-6,6-7 |
| Challenger Cary | 2023/09/11 17:00 | Strong Kirchheimer v Alex Rybakov | 6-7,7-5,7-6 |
| Challenger Cary | 2023/09/10 17:25 | Strong Kirchheimer v Thomson, Connor | 7-6,6-3 |
| Winston-Salem, USA | 2023/08/22 19:20 | Dominik Koepfer v Strong Kirchheimer | 6-3,6-2 |
| Winston-Salem, USA | 2023/08/20 17:00 | Strong Kirchheimer v Darian King | 6-2,4-6,6-7 |
| Winston-Salem, USA | 2023/08/19 16:25 | Adam Walton v Strong Kirchheimer | 5-7,3-6 |
| Challenger Winnipeg | 2023/08/15 20:50 | Strong Kirchheimer v Liam Broady | 3-6,3-6 |
| Challenger Winnipeg | 2023/08/14 18:20 | Strong Kirchheimer v Alafia Ayeni | 7-5,6-2 |
| Challenger Winnipeg | 2023/08/13 18:45 | Strong Kirchheimer v Juan Carlos Aguilar | 1-6,6-4,6-4 |