Stadium: Grossman-Kennedy Stadium Round: 27 Ground: Hardcourt outdoor
| Challenger Cali | 2023/06/19 21:05 | Tristan Schoolkate v Thai-Son Kwiatkowski | 7-6,7-5 |
| Challenger Tiburon | 2023/10/05 23:30 | Alex Michelsen v Thai-Son Kwiatkowski | 6-4,4-6,3-6 |
| Challenger Tiburon | 2023/10/03 18:35 | Giovanni Mpetshi Perricard v Thai-Son Kwiatkowski | 6-7,3-6 |
| Challenger Tiburon | 2023/10/02 17:00 | Federico Agustin Gomez v Thai-Son Kwiatkowski | 6-7,1-6 |
| Challenger Tiburon | 2023/10/01 18:35 | Thai-Son Kwiatkowski v Elmer Moller | 6-3,6-2 |
| Challenger Charleston | 2023/09/27 14:00 | Christian Harrison v Thai-Son Kwiatkowski | 6-7,7-6,6-2 |
| Challenger Charleston | 2023/09/25 16:55 | Skander Mansouri v Thai-Son Kwiatkowski | 6-3,2-6,5-7 |
| Challenger Charleston | 2023/09/24 16:40 | Donald Young v Thai-Son Kwiatkowski | 4-6,4-6 |
| Challenger Cary | 2023/09/13 17:30 | William Jansen v Thai-Son Kwiatkowski | 4-6,3-6 |
| Challenger Tiburon | 2023/10/05 21:05 | Tristan Schoolkate v Ryan Peniston | 6-3,6-4 |
| Challenger Tiburon | 2023/10/03 17:00 | Ozan Baris v Tristan Schoolkate | 3-6,1-6 |
| Challenger Charleston | 2023/09/27 14:00 | Tristan Schoolkate v Denis Kudla | 4-6,5-7 |
| Challenger Columbus | 2023/09/22 16:00 | Tristan Schoolkate v Denis Kudla | 2-6,4-6 |
| Challenger Columbus | 2023/09/20 20:20 | Adam Walton v Tristan Schoolkate | 6-4,3-6,1-6 |
| Challenger Columbus | 2023/09/18 22:55 | Tristan Schoolkate v Abedallah Shelbayh | 6-4,6-3 |
| Challenger Cary | 2023/09/12 19:35 | Tristan Schoolkate v Strong Kirchheimer | 7-6,3-6,6-7 |
| Challenger Lexington | 2023/08/03 18:20 | Aidan Mayo v Tristan Schoolkate | 3-6,6-4,6-3 |