Stadium: Court 1 Round: 26 Ground: Hardcourt indoor
| Challenger Fairfield | 2023/10/09 19:15 | Strong Kirchheimer v Ethan Quinn | 7-6,7-5 |
| Challenger Champaign | 2023/11/14 16:00 | Emilio Nava v Ethan Quinn | 3-6,2-6 |
| Challenger Knoxville | 2023/11/07 15:00 | Tennys Sandgren v Ethan Quinn | 4-6,7-6,7-6 |
| Challenger Charlottesville | 2023/11/04 19:25 | Aidan Mayo v Ethan Quinn | 3-6,6-4,6-3 |
| 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 Knoxville | 2023/11/07 20:20 | Thai-Son Kwiatkowski v Strong Kirchheimer | 6-7,6-2,6-4 |
| ITF M25 Saint-Augustin | 2023/10/28 17:15 | Strong Kirchheimer v Charles Broom | 4-6,2-6 |
| ITF M25 Saint-Augustin | 2023/10/27 23:15 | Kiranpal Pannu v Strong Kirchheimer | 1-6,1-6 |
| ITF M25 Saint-Augustin | 2023/10/26 14:55 | Osgar O'Hoisin v Strong Kirchheimer | 2-6,2-6 |
| ITF M25 Saint-Augustin | 2023/10/25 16:05 | Jonathan Sorbo v Strong Kirchheimer | 0-6,0-6 |
| Challenger Fairfield | 2023/10/10 19:15 | Christian Langmo v Strong Kirchheimer | 6-4,6-4 |
| Challenger Fairfield | 2023/10/09 19:15 | Strong Kirchheimer v Ethan Quinn | 7-6,7-5 |
| Challenger Fairfield | 2023/10/08 22:20 | Strong Kirchheimer v Evan Burnett | 6-2,6-2 |