| UTR Pro Tennis Series Florida | 2021/01/17 14:00 | Joshua Sheehy v Mei, Mesa | 6-2,4-6,5-7 |
| UTR Pro Tennis Series Florida | 2021/01/16 18:00 | Nick Chappell v Joshua Sheehy | 3-6,0-0 |
| UTR Pro Tennis Series Florida | 2021/01/15 14:00 | Joshua Sheehy v Jachuck, Ronan | 6-2,6-4 |
| UTR Pro Tennis Series Florida | 2021/01/14 14:57 | Aditya Vashistha v Joshua Sheehy | 6-7,6-3,5-0 |
| UTR Pro Tennis Series Florida | 2021/01/12 18:00 | Daniel Milavsky v Joshua Sheehy | 3-6,3-5 |
| UTR Pro Tennis Series Florida | 2021/01/11 17:00 | Joshua Sheehy v Carnevale-Miino, Tommaso | 6-4,6-4 |
| Fayetteville, AR, Singles Qualifying, M-ITF-USA-31 | 2020/11/03 16:00 | Zink, Tyler v Joshua Sheehy | 7-6,6-2 |
| Fayetteville, AR, Singles Qualifying, M-ITF-USA-31 | 2020/11/02 17:30 | Joshua Sheehy v Mesquida Berg, Oscar | 7-6,3-6,10-8 |
| ITF - M15 Santo Domingo | 2020/12/09 13:30 | Nick Chappell v Volfson, David | 6-1,6-1 |
| ITF - M15 Santo Domingo | 2020/12/08 13:30 | Volfson, David v Ansari, Austin Ansari | 6-1,6-3 |
| ITF - M15 Santo Domingo | 2020/12/07 14:00 | Volfson, David v Rowland Phillips | 6-2,6-2 |
| ITF - M15 Santo Domingo | 2020/12/01 13:30 | Volfson, David v Rowland Phillips | 6-7,6-1,1-10 |
| ITF - M15 Santo Domingo | 2020/11/30 15:00 | Volfson, David v Angel J Maleno Rosario | 6-0,6-1 |
| ITF M15 Quinta Do Lago | 2020/11/05 10:00 | Volfson, David v Matteo Arnaldi | 1-6,5-7 |
| ITF M15 Quinta Do Lago | 2020/11/04 12:50 | Khumoyun Sultanov v Volfson, David | 3-6,6-7 |
| ITF M15 Quinta Do Lago | 2020/11/03 09:30 | Volfson, David v Tiago Torres | 6-3,4-6,10-7 |