Stadium: Tad Taube Court Round: 27 Ground: Hardcourt outdoor
| 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 |
| Challenger Cary | 2023/09/16 21:00 | Zachary Svajda v Alex Michelsen | 6-3,7-5 |
| Challenger Cary | 2023/09/15 21:00 | Guido Andreozzi v Alex Michelsen | 3-6,5-7 |
| Challenger Cary | 2023/09/13 23:20 | Strong Kirchheimer v Alex Michelsen | 3-6,1-6 |
| Challenger Cary | 2023/09/12 18:45 | Maxime Janvier v Alex Michelsen | 7-5,6-7,3-6 |
| 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 Tiburon | 2023/10/01 17:00 | Christian Langmo v Nishesh Basavareddy | 3-6,4-6 |
| Challenger Columbus | 2023/09/20 16:00 | Nishesh Basavareddy v Vasek Pospisil | 5-7,6-2,5-7 |
| ITF M25 - Champaign | 2023/07/19 19:05 | Jack Anthrop v Nishesh Basavareddy | 4-6,5-7 |
| Challenger Chicago | 2023/07/13 20:05 | Jason Jung v Nishesh Basavareddy | 3-6,7-6,6-2 |
| Challenger Chicago | 2023/07/12 19:30 | Nishesh Basavareddy v Steve Johnson | 6-3,2-6,6-4 |