Stadium: Brenda Meyers Court Round: 25 Ground: Hardcourt indoor
| 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 |
| Challenger Bogota | 2023/09/27 18:25 | Cannon Kingsley v David Jorda Sanchis | 4-6,6-3,4-6 |
| Challenger Columbus | 2023/09/23 17:30 | Alexis Galarneau v Cannon Kingsley | 6-4,7-6 |
| Challenger Columbus | 2023/09/22 17:25 | Cannon Kingsley v Christian Harrison | 7-5,6-4 |
| Challenger Columbus | 2023/09/21 17:45 | James Trotter v Cannon Kingsley | 4-6,7-6,3-6 |
| 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 |
| 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 |