stadio: Court 1 Round: 27 Ground: Hardcourt indoor
| Challenger Champaign | 2023/11/16 17:00 | Martin Damm v Mats Rosenkranz | 6-3,6-4 |
| Challenger Champaign | 2023/11/14 22:35 | Martin Damm v Alfredo Perez | 7-6,6-4 |
| Challenger Knoxville | 2023/11/08 16:00 | Martin Damm v Denis Kudla | 6-7,3-6 |
| Challenger Knoxville | 2023/11/06 20:00 | Michael Mmoh v Martin Damm | 4-6,3-6 |
| Challenger Charlottesville | 2023/11/01 17:15 | Nino Serdarusic v Martin Damm | 7-6,3-6,6-1 |
| Challenger Charlottesville | 2023/10/30 23:20 | Martin Damm v Zachary Svajda | 2-6,6-3,7-6 |
| Challenger Bratislava | 2023/10/14 14:10 | Gabriel Diallo v Martin Damm | 7-6,6-2 |
| Challenger Bratislava | 2023/10/13 18:00 | Martin Damm v Maxime Cressy | 6-4,7-6 |
| Challenger Champaign | 2023/11/16 18:20 | Sebastian Fanselow v Alex Michelsen | 3-6,2-6 |
| Challenger Champaign | 2023/11/15 01:25 | Bernard Tomic v Alex Michelsen | 4-6,0-6 |
| Challenger Knoxville | 2023/11/12 18:00 | Denis Kudla v Alex Michelsen | 5-7,6-4,2-6 |
| Challenger Knoxville | 2023/11/11 18:25 | Alex Michelsen v Tennys Sandgren | 6-2,2-6,6-4 |
| Challenger Knoxville | 2023/11/10 19:05 | Nishesh Basavareddy v Alex Michelsen | 3-6,3-6 |
| Challenger Knoxville | 2023/11/08 17:50 | Gabriel Debru v Alex Michelsen | 3-6,6-3,4-6 |
| Challenger Knoxville | 2023/11/07 00:55 | Bernard Tomic v Alex Michelsen | 6-4,6-7,4-6 |
| Challenger Charlottesville | 2023/10/31 18:45 | Cannon Kingsley v Alex Michelsen | 7-5,6-3 |