| UTR Pro Tennis Series Florida | 2021/01/21 14:00 | Joshua Sheehy v Sullivan, Charles | 3-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/01/23 14:00 | Sullivan, Charles v Perego, Giulio | 4-6,2-6 |
| UTR Pro Tennis Series Florida | 2021/01/22 16:00 | Arconada, Jordi v Sullivan, Charles | 4-6,2-6 |
| UTR Pro Tennis Series Florida | 2021/01/21 14:00 | Joshua Sheehy v Sullivan, Charles | 3-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/01/20 14:00 | Volfson, David v Sullivan, Charles | 7-6,4-6,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/18 15:30 | Matija Pecotic v Sullivan, Charles | 6-2,6-2 |
| UTR Pro Tennis Series Florida | 2021/01/16 14:00 | Sullivan, Charles v Scott, Fletcher | 6-4,6-7,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/14 20:13 | Sullivan, Charles v Gabrielius Guzauskas | 7-5,3-0 |
| UTR Pro Tennis Series Florida | 2021/01/13 16:00 | Harris Walker v Sullivan, Charles | 6-4,5-4 |
| UTR Pro Tennis Series California | 2021/02/28 17:30 | Colton Smith v Joshua Sheehy | 6-4,6-4 |
| UTR Pro Tennis Series California | 2021/02/27 20:30 | Joshua Sheehy v Boyer, Dusty H | 7-6,0-0 |
| UTR Pro Tennis Series California | 2021/02/26 20:00 | Joshua Sheehy v Barrientos, Nicolas | 5-7,4-5 |
| UTR Pro Tennis Series California | 2021/02/25 16:00 | Joshua Sheehy v Spencer Johnson | 6-2,5-3 |
| UTR Pro Tennis Series California | 2021/02/24 18:00 | Hovhannisyan, Mousheg v Joshua Sheehy | 6-4,6-4 |
| UTR Pro Tennis Series California | 2021/02/23 20:00 | Baker, Blu v Joshua Sheehy | 7-6,5-2 |
| UTR Pro Tennis Series California | 2021/02/20 19:00 | Spencer Johnson v Joshua Sheehy | 6-3,6-3 |
| UTR Pro Tennis Series California | 2021/02/18 16:00 | Joshua Sheehy v Alex Jones | 7-6,5-1 |