Stadium: Court 2 Round: 14 Ground: Hardcourt outdoor
| Challenger Tiburon | 2019/09/25 18:55 | Ulises Blanch v Darian King | 6-2,6-7,5-7 |
| Challenger Winnipeg | 2023/08/17 18:45 | Darian King v Ryan Peniston | 0-6,1-6 |
| Challenger Winnipeg | 2023/08/16 17:00 | Benjamin Bonzi v Darian King | 3-6,1-6 |
| Challenger Winnipeg | 2023/08/15 16:00 | Darian King v Brayden Schnur | 6-2,6-1 |
| Challenger Winnipeg | 2023/08/14 18:50 | Matija Pecotic v Darian King | 3-6,4-6 |
| Challenger Winnipeg | 2023/08/13 22:05 | Joshua Sheehy v Darian King | 6-3,1-6,3-6 |
| ITF M15 Pittsburgh | 2023/07/30 18:45 | Darian King v Juan Carlos Aguilar | 4-6,6-3,6-3 |
| ITF M15 Pittsburgh | 2023/07/29 16:30 | Darian King v Samir Banerjee | 6-4,7-6 |
| ITF M15 Pittsburgh | 2023/07/28 16:50 | Kyle Seelig v Darian King | 3-6,0-6 |
| Challenger Winnipeg | 2023/08/16 20:45 | Ulises Blanch v Arthur Cazaux | 3-6,5-7 |
| Challenger Winnipeg | 2023/08/15 20:10 | Andres Martin v Ulises Blanch | 6-7,6-7 |
| Challenger Winnipeg | 2023/08/14 16:00 | Ulises Blanch v Andrew Fenty | 6-3,1-6,6-4 |
| 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 |