Stadium: Estadio 4 Round: 25 Ground: Clay
| 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 M25 Dallas | 2023/07/11 19:25 | Karl Poling v Joshua Sheehy | 6-4,3-6,6-3 |
| ITF M15 Los Angeles | 2023/06/21 00:30 | Joshua Sheehy v Nicholas Godsick | 2-6,5-7 |
| ITF M25 Padova | 2023/07/13 19:25 | Gonzalo Bueno v Giorgio Tabacco | 0-6,2-6 |
| ITF M25 Padova | 2023/07/11 13:50 | Gonzalo Bueno v Luca Fantini | 7-5,6-3 |
| Challenger Milan | 2023/07/06 16:15 | Gonzalo Bueno v Luciano Darderi | 6-7,1-6 |
| ITF M25 Cattolica | 2023/06/22 12:00 | Gonzalo Bueno v Julian Ocleppo | 6-0,6-4 |
| ITF M25 Cattolica | 2023/06/21 12:00 | Gonzalo Bueno v Andrea Picchione | 6-4,6-2 |
| ITF M25 Cattolica | 2023/06/20 09:50 | Gonzalo Bueno v Carlo A Caniato | 6-4,6-4 |
| ITF M25 Risskov/Aarhus | 2023/06/13 08:30 | Gonzalo Bueno v Henrik Heise Korsgaard | 5-7,7-6,2-6 |
| Challenger Prostejov | 2023/06/04 08:00 | Pol Martin Tiffon v Gonzalo Bueno | 6-0,6-1 |