Stadium: Court 2 Round: 19 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2023/08/13 22:30 | Matija Pecotic v Alex Rybakov | 6-2,6-2 |
| ATP Toronto | 2023/08/06 18:15 | Matteo Arnaldi v Matija Pecotic | 6-4,6-4 |
| ATP Toronto | 2023/08/05 19:55 | Ilya Ivashka v Matija Pecotic | 2-6,6-7 |
| Challenger Salinas | 2023/07/29 16:00 | Matija Pecotic v Illya Marchenko | 4-6,4-6 |
| Challenger Salinas | 2023/07/28 16:30 | Matija Pecotic v Altug Celikbilek | 7-5,6-1 |
| Challenger Salinas | 2023/07/27 15:00 | Omar Jasika v Matija Pecotic | 3-6,5-7 |
| Challenger Salinas | 2023/07/26 17:55 | Matija Pecotic v Dane Sweeny | 7-6,6-1 |
| Challenger Salinas | 2023/07/25 16:50 | Tristan Schoolkate v Matija Pecotic | 5-7,6-7 |
| Challenger Winnipeg | 2023/08/13 22:05 | Joshua Sheehy v Darian King | 6-3,1-6,3-6 |
| ITF - Pittsburgh M15 | 2023/07/30 18:45 | Darian King v Juan Carlos Aguilar | 4-6,6-3,6-3 |
| ITF - Pittsburgh M15 | 2023/07/29 16:30 | Darian King v Samir Banerjee | 6-4,7-6 |
| ITF - Pittsburgh M15 | 2023/07/28 16:50 | Kyle Seelig v Darian King | 3-6,0-6 |
| ITF - Pittsburgh M15 | 2023/07/27 17:15 | Ryan Dickerson v Darian King | 7-5,1-6,1-6 |
| ITF - Pittsburgh M15 | 2023/07/26 17:15 | Juan Sebastian Osorio v Darian King | 1-6,4-6 |
| ITF - Rochester M15 | 2023/07/23 17:00 | Ignacio Monzon v Darian King | 0-6,6-7 |
| ITF - Rochester M15 | 2023/07/22 16:00 | Tyler Stice v Darian King | 1-6,3-6 |