Stadium: Brenda Meyers Court Round: 28 Ground: Hardcourt indoor
| Challenger Tiburon | 2023/10/01 19:40 | Ethan Quinn v Aidan Mayo | 4-6,4-6 |
| Challenger Charleston | 2023/09/28 17:45 | Ethan Quinn v Aidan Mayo | 7-5,7-5 |
| Challenger Charlottesville | 2023/11/03 18:55 | Alexander Ritschard v Aidan Mayo | 3-6,4-6 |
| Challenger Charlottesville | 2023/10/31 19:25 | Aidan Mayo v Alafia Ayeni | 7-5,6-2 |
| Challenger Charlottesville | 2023/10/30 17:30 | Aidan Mayo v Christian Harrison | 2-6,7-5,6-2 |
| Challenger Charlottesville | 2023/10/29 23:05 | Aidan Mayo v Douglas Yaffa | 6-2,6-2 |
| ITF M25 Saint-Augustin | 2023/10/28 15:00 | Mohamed Aziz Dougaz v Aidan Mayo | 6-3,7-6 |
| ITF M25 Saint-Augustin | 2023/10/27 19:10 | Aidan Mayo v Giles Hussey | 7-6,7-6 |
| ITF M25 Saint-Augustin | 2023/10/26 22:30 | Aidan Mayo v Keenan Mayo | 6-1,7-5 |
| ITF M25 Saint-Augustin | 2023/10/25 16:45 | Aidan Mayo v Colin Markes | 6-2,6-4 |
| Challenger Charlottesville | 2023/11/03 22:00 | Benoit Paire v Ethan Quinn | 6-7,2-6 |
| Challenger Charlottesville | 2023/11/02 16:00 | Ethan Quinn v Emilio Nava | 6-3,6-1 |
| Challenger Charlottesville | 2023/10/31 14:00 | Ethan Quinn v Mitchell Krueger | 3-6,7-6,6-4 |
| Challenger Charlottesville | 2023/10/30 14:00 | Ethan Quinn v Dylan Dietrich | 7-6,6-3 |
| Challenger Charlottesville | 2023/10/29 14:00 | Ethan Quinn v James Hopper | 6-0,6-3 |
| Challenger Fairfield | 2023/10/09 19:15 | Strong Kirchheimer v Ethan Quinn | 7-6,7-5 |
| Challenger Fairfield | 2023/10/08 21:35 | Kiranpal Pannu v Ethan Quinn | 2-6,7-6,4-6 |
| Challenger Tiburon | 2023/10/01 19:40 | Ethan Quinn v Aidan Mayo | 4-6,4-6 |