Stadium: Court 3 Round: 25 Ground: Hardcourt indoor
| Challenger Knoxville | 2023/11/06 17:35 | Sebastian Fanselow v Alex Rybakov | 6-7,6-4,6-4 |
| Challenger Knoxville | 2023/11/05 19:00 | Sebastian Fanselow v Kyle Kang | 6-3,6-3 |
| Challenger Charlottesville | 2023/10/30 15:50 | Sebastian Fanselow v Darian King | 3-6,2-6 |
| Challenger Charlottesville | 2023/10/29 20:25 | Sebastian Fanselow v Fons Van Sambeek | 6-0,6-1 |
| ITF - Tavira M25 | 2023/10/23 12:00 | Sebastian Fanselow v Henrique Rocha | 6-2,6-3 |
| ITF - Tavira M25 | 2023/10/21 11:35 | Martin Landaluce v Sebastian Fanselow | 6-3,2-6,2-6 |
| ITF - Tavira M25 | 2023/10/20 13:00 | Sebastian Fanselow v Twan Van Zijl | 6-0,6-1 |
| ITF - Tavira M25 | 2023/10/19 12:00 | Sebastian Fanselow v Tiago Pereira | 6-0,7-5 |
| Challenger Knoxville | 2023/11/06 18:00 | Cannon Kingsley v Gabi Adrian Boitan | 7-5,6-3 |
| Challenger Knoxville | 2023/11/05 22:15 | Cannon Kingsley v Alex Lawson | 6-4,7-6 |
| Challenger Charlottesville | 2023/11/01 19:40 | Brandon Holt v Cannon Kingsley | 6-4,6-4 |
| Challenger Charlottesville | 2023/10/31 18:45 | Cannon Kingsley v Alex Michelsen | 7-5,6-3 |
| Challenger Fairfield | 2023/10/08 18:45 | Learner Tien v Cannon Kingsley | 6-4,6-4 |
| Challenger Tiburon | 2023/10/03 18:40 | Tennys Sandgren v Cannon Kingsley | 6-4,6-4 |
| Challenger Tiburon | 2023/10/02 18:40 | Cannon Kingsley v Trevor Svajda | 6-3,4-6,6-1 |
| Challenger Tiburon | 2023/10/01 23:25 | Brandon Holt v Cannon Kingsley | 6-3,1-6,3-6 |