Stadium: Cancha 11 Round: 14 Ground: Clay
| ITF M15 Tabasco | 2023/05/22 23:00 | Joshua Sheehy v Justin Roberts | 6-3,6-3 |
| ITF M15 Tacarigua | 2023/04/18 23:20 | Justin Roberts v Joshua Sheehy | 6-2,7-6 |
| Challenger Winnipeg | 2023/08/13 22:05 | Joshua Sheehy v Darian King | 6-3,1-6,3-6 |
| 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 |
| Challenger Santo Domingo | 2023/08/09 01:10 | Joao Lucas Reis da Silva v Justin Roberts | 6-4,6-4 |
| Challenger Santo Domingo | 2023/08/08 14:00 | Conner Huertas Del Pino v Justin Roberts | 6-7,4-6 |
| Challenger Santo Domingo | 2023/08/06 17:00 | Preston Brown v Justin Roberts | 6-7,4-6 |
| Challenger Lexington | 2023/07/31 14:00 | Philip Sekulic v Justin Roberts | 6-1,6-4 |
| Challenger Lexington | 2023/07/30 15:05 | Justin Roberts v Ramkumar Ramanathan | 7-6,7-6 |
| ITF M15 Rochester | 2023/07/21 18:50 | Ignacio Monzon v Justin Roberts | 6-4,6-2 |
| ITF M15 Rochester | 2023/07/20 15:25 | Yannik Rahman v Justin Roberts | 1-6,2-6 |
| ITF M15 Rochester | 2023/07/19 14:30 | Maksim Tikhomirov v Justin Roberts | 1-6,4-6 |