Stadium: Court 2 Round: 14 Ground: Hardcourt outdoor
| Challenger Santo Domingo | 2023/08/09 16:00 | Joshua Sheehy v Gonzalo Bueno | 6-7,3-6 |
| Challenger Santo Domingo | 2023/08/08 15:10 | James Trotter v Joshua Sheehy | 6-1,3-6,4-6 |
| Challenger Santo Domingo | 2023/08/06 20:50 | Enmanuel Munoz v Joshua Sheehy | 5-7,4-6 |
| Challenger Lexington | 2023/07/30 14:00 | Justin Boulais v Joshua Sheehy | 6-2,7-5 |
| Challenger Granby | 2023/07/18 16:25 | Tristan Schoolkate v Joshua Sheehy | 6-2,6-3 |
| Challenger Granby | 2023/07/17 14:00 | Joshua Sheehy v Colin Markes | 6-2,6-7,7-5 |
| Challenger Granby | 2023/07/16 17:40 | Calum Puttergill v Joshua Sheehy | 4-6,6-7 |
| ITF - Dallas M25 | 2023/07/11 19:25 | Karl Poling v Joshua Sheehy | 6-4,3-6,6-3 |
| 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 |
| ITF - Rochester M15 | 2023/07/21 19:00 | Henrik Wiersholm v Darian King | 7-6,3-6,4-6 |