Stadium: Court 2 Round: 25 Ground: Hardcourt indoor
| Challenger Champaign | 2023/11/13 16:00 | Mark Whitehouse v Keegan Smith | 7-6,7-6 |
| Challenger Champaign | 2023/11/12 16:00 | Gabi Adrian Boitan v Mark Whitehouse | 6-4,1-6,4-6 |
| ITF M25 Austin | 2023/11/09 14:55 | Mark Whitehouse v Colin Markes | 6-1,5-7,6-10 |
| ITF M25 Austin | 2023/11/08 20:35 | Mark Whitehouse v Marko Mesarovic | 5-7,7-5,6-3 |
| ITF M15 Fayetteville | 2023/11/01 18:00 | Mark Whitehouse v Olle Wallin | 7-6,5-7,6-7 |
| ITF M15 Norman | 2023/10/25 18:15 | Mark Whitehouse v Tyler Stice | 1-6,6-3,3-6 |
| ITF M15 Las Vegas | 2023/10/18 19:15 | Adit Sinha v Mark Whitehouse | 7-5,6-2 |
| Challenger Fairfield | 2023/10/08 17:00 | Evan Zhu v Mark Whitehouse | 6-2,6-2 |
| Challenger Knoxville | 2023/11/07 15:00 | Denis Kudla v Patrick Kypson | 6-7,6-3,6-4 |
| Challenger Charlottesville | 2023/11/04 17:30 | Beibit Zhukayev v Patrick Kypson | 6-4,7-6 |
| Challenger Charlottesville | 2023/11/03 16:00 | Patrick Kypson v Brandon Holt | 6-1,6-4 |
| Challenger Charlottesville | 2023/11/01 18:20 | Denis Kudla v Patrick Kypson | 1-6,3-6 |
| Challenger Charlottesville | 2023/10/30 19:30 | Patrick Kypson v Gabriel Debru | 6-4,7-5 |
| Challenger Fairfield | 2023/10/09 20:45 | Patrick Kypson v Aidan Mayo | 6-3,6-7,6-7 |
| Challenger Tiburon | 2023/10/02 22:35 | Alexis Galarneau v Patrick Kypson | 7-6,6-4 |
| Challenger Charleston | 2023/09/27 16:10 | Patrick Kypson v Ryan Peniston | 2-6,4-6 |