Stadium: Stadium Round: 26 Ground: Hardcourt outdoor
| 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 - Winnipeg | 2023/08/14 18:20 | Strong Kirchheimer v Alafia Ayeni | 7-5,6-2 |
| Challenger - Cary | 2023/09/12 18:45 | Maxime Janvier v Alex Michelsen | 7-5,6-7,3-6 |
| US Open | 2023/08/31 20:00 | Nicolas Jarry v Alex Michelsen | 4-6,6-3,6-3,6-3 |
| US Open | 2023/08/29 16:40 | Albert Ramos-Vinolas v Alex Michelsen | 4-6,3-6,4-6 |
| ATP - Winston-Salem | 2023/08/24 01:50 | Laslo Djere v Alex Michelsen | 6-4,6-4 |
| ATP - Winston-Salem | 2023/08/22 18:00 | Alex Michelsen v Sebastian Ofner | 7-6,7-5 |
| ATP - Winston-Salem | 2023/08/20 22:30 | Alex Michelsen v Juan Pablo Varillas | 6-3,6-7,6-0 |
| Challenger - Stanford | 2023/08/15 20:35 | Borna Gojo v Alex Michelsen | 4-6,6-4,7-6 |
| Challenger - Stanford | 2023/08/14 05:00 | Alex Michelsen v Seong Chan Hong | 4-6,6-2,6-0 |