Stadium: Court 2 Round: 27 Ground: Hardcourt indoor
| Challenger - Fairfield | 2023/10/13 18:30 | Alex Michelsen v Nishesh Basavareddy | 3-6,3-6 |
| Challenger - Knoxville | 2023/11/09 17:00 | Beibit Zhukayev v Nishesh Basavareddy | 4-6,2-6 |
| Challenger - Knoxville | 2023/11/07 19:20 | Mats Rosenkranz v Nishesh Basavareddy | 6-4,2-6,5-7 |
| Challenger - Fairfield | 2023/10/15 19:00 | Nishesh Basavareddy v Zachary Svajda | 4-6,1-6 |
| Challenger - Fairfield | 2023/10/14 21:25 | Nishesh Basavareddy v Steve Johnson | 3-6,7-5,6-3 |
| Challenger - Fairfield | 2023/10/13 18:30 | Alex Michelsen v Nishesh Basavareddy | 3-6,3-6 |
| Challenger - Fairfield | 2023/10/10 23:20 | Nishesh Basavareddy v Adam Walton | 6-3,7-5 |
| Challenger - Tiburon | 2023/10/06 23:15 | Nishesh Basavareddy v Zachary Svajda | 0-6,2-6 |
| Challenger - Tiburon | 2023/10/02 17:00 | Nishesh Basavareddy v Aidan Mayo | 7-5,7-5 |
| 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 |
| Challenger - Fairfield | 2023/10/13 18:30 | Alex Michelsen v Nishesh Basavareddy | 3-6,3-6 |
| Challenger - Fairfield | 2023/10/12 17:00 | Alex Michelsen v Thai-Son Kwiatkowski | 6-3,6-4 |
| Challenger - Fairfield | 2023/10/10 18:50 | Alex Michelsen v Mohamed Aziz Dougaz | 2-6,7-6,6-0 |
| Challenger - Tiburon | 2023/10/05 23:30 | Alex Michelsen v Thai-Son Kwiatkowski | 6-4,4-6,3-6 |
| Challenger - Tiburon | 2023/10/03 20:20 | Alex Michelsen v Brayden Schnur | 6-7,6-3,6-4 |