Stadium: Court 3 Round: 14 Ground: Hardcourt indoor
| Challenger Cary | 2023/09/13 23:20 | Strong Kirchheimer v Alex Michelsen | 3-6,1-6 |
| Challenger Cary | 2023/09/12 19:35 | Tristan Schoolkate v Strong Kirchheimer | 7-6,3-6,6-7 |
| 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 Connor Thomson | 7-6,6-3 |
| ATP Winston-Salem | 2023/08/22 19:20 | Dominik Koepfer v Strong Kirchheimer | 6-3,6-2 |
| ATP Winston-Salem | 2023/08/20 17:00 | Strong Kirchheimer v Darian King | 6-2,4-6,6-7 |
| ATP Winston-Salem | 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 Cary | 2023/09/11 17:00 | Donald Young v Kiranpal Pannu | 6-4,6-1 |
| Challenger Cary | 2023/09/10 17:25 | Kiranpal Pannu v Quinn Vandecasteele | 6-2,4-6,6-0 |
| Challenger Winnipeg | 2023/08/15 18:45 | Kiranpal Pannu v Arthur Cazaux | 3-6,1-6 |
| Challenger Winnipeg | 2023/08/14 16:00 | Kiranpal Pannu v Tatsuma Ito | 7-5,4-6,6-1 |
| Challenger Winnipeg | 2023/08/13 16:00 | Keenan Mayo v Kiranpal Pannu | 1-6,4-6 |
| Challenger Santo Domingo | 2023/08/06 20:20 | John-Patrick Smith v Kiranpal Pannu | 3-6,7-6,6-1 |
| ATP Washington | 2023/07/31 18:40 | Aslan Karatsev v Kiranpal Pannu | 7-6,6-1 |
| ATP Washington | 2023/07/30 15:35 | Kiranpal Pannu v Bruno Kuzuhara | 3-6,6-2,7-6 |