Stadium: Court 1 Round: 19 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2023/08/13 17:30 | Ulises Blanch v Benjamin Sigouin | 6-2,6-1 |
| Challenger - Lexington | 2023/08/04 15:00 | Ulises Blanch v Steve Johnson | 3-6,4-6 |
| Challenger - Lexington | 2023/08/02 14:00 | Adam Walton v Ulises Blanch | 3-6,3-6 |
| Challenger - Lexington | 2023/08/01 14:00 | Aidan Mchugh v Ulises Blanch | 6-7,4-6 |
| Challenger - Segovia | 2023/07/24 14:25 | Ulises Blanch v John Echeverria | 4-6,7-6,6-7 |
| Challenger - Segovia | 2023/07/23 12:00 | Ulises Blanch v Pablo Carretero | 6-3,6-1 |
| Challenger - Pozoblanco | 2023/07/17 19:35 | Daniel Cukierman v Ulises Blanch | 6-4,6-4 |
| Challenger - Pozoblanco | 2023/07/16 20:40 | Vilius Gaubas v Ulises Blanch | 4-6,3-6 |
| Challenger Winnipeg | 2023/08/13 17:35 | Andrew Fenty v James Trotter | 6-4,2-6,7-6 |
| ITF M25 Southaven | 2023/08/10 16:25 | Andrew Fenty v Michael Zheng | 3-6,0-6 |
| ITF M25 Southaven | 2023/08/08 18:30 | Andrew Fenty v Taha Baadi | 6-3,6-4 |
| ATP Washington | 2023/07/29 15:50 | Brandon Holt v Andrew Fenty | 7-5,6-3 |
| ITF M25 Champaign | 2023/07/19 19:45 | Andrew Fenty v Alexander Bernard | 6-4,3-6,6-7 |
| ITF M25 Champaign | 2023/07/18 15:00 | Kareem Allaf v Andrew Fenty | 1-6,2-6 |
| Challenger Chicago | 2023/07/09 17:20 | Yunseong Chung v Andrew Fenty | 7-5,6-2 |
| Challenger Bloomfield Hills | 2023/07/03 20:00 | Omar Jasika v Andrew Fenty | 6-3,6-4 |