Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| Challenger - Chicago | 2023/07/13 18:20 | Tristan Schoolkate v Ethan Quinn | 6-4,3-6,2-6 |
| Challenger - Chicago | 2023/07/11 15:00 | Altug Celikbilek v Tristan Schoolkate | 4-6,6-7 |
| Challenger - Chicago | 2023/07/10 16:40 | Tristan Schoolkate v Christian Langmo | 6-3,1-6,7-5 |
| Challenger - Chicago | 2023/07/09 21:30 | Tristan Schoolkate v Mukund Sasikumar | 6-4,6-1 |
| Challenger - Bloomfield Hills | 2023/07/08 15:00 | Tristan Schoolkate v Steve Johnson | 4-6,2-6 |
| Challenger - Bloomfield Hills | 2023/07/07 15:00 | Omar Jasika v Tristan Schoolkate | 4-6,3-6 |
| Challenger - Bloomfield Hills | 2023/07/06 18:15 | Tristan Schoolkate v Altug Celikbilek | 7-6,7-5 |
| Challenger - Bloomfield Hills | 2023/07/05 14:00 | Evan Zhu v Tristan Schoolkate | 7-6,2-6,4-6 |
| 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 - M15 San Diego | 2023/06/13 21:00 | A.J Catanzariti v Joshua Sheehy | 3-6,7-5,6-4 |
| ITF - M15 Tabasco | 2023/05/26 17:00 | Ezekiel Clark v Joshua Sheehy | 6-3,6-7,7-6 |
| ITF - M15 Tabasco | 2023/05/25 17:00 | Joshua Sheehy v Andres Andrade | 4-6,6-4,6-4 |
| ITF - M15 Tabasco | 2023/05/24 16:00 | Jorge Panta v Joshua Sheehy | 3-6,6-7 |