| UTR Pro Tennis Series Cancun | 2021/04/01 14:30 | Joshua Sheehy v Wilson Leite | 6-7,6-4,5-6 |
| UTR Pro Tennis Series Cancun | 2021/03/31 15:00 | Joshua Sheehy v Jean-Baptiste Badon | 6-4,7-5 |
| UTR Pro Tennis Series Cancun | 2021/03/30 13:00 | Joshua Sheehy v Juan Sebastian Gomez | 2-6,1-5 |
| UTR Pro Tennis Series Cancun | 2021/03/29 13:30 | Joshua Sheehy v Gage Brymer | 6-7,0-6 |
| UTR Pro Tennis Series Florida | 2021/03/14 14:30 | Harris Walker v Joshua Sheehy | 7-6,5-4 |
| UTR Pro Tennis Series Florida | 2021/03/13 14:00 | Joshua Sheehy v Giulio Perego | 6-2,5-4 |
| UTR Pro Tennis Series Florida | 2021/03/12 17:00 | Joshua Sheehy v Murphy Cassone | 6-2,6-2 |
| UTR Pro Tennis Series Florida | 2021/03/10 18:00 | Joshua Sheehy v Kiranpal Pannu | 6-4,3-6,2-6 |
| UTR Pro Tennis Series Cancun | 2021/04/02 16:00 | Drew Van Orderlain v Mateo Gomez | 7-6,1-6,7-6 |
| UTR Pro Tennis Series Cancun | 2021/04/01 13:00 | Drew Van Orderlain v Jorge Panta | 1-6,1-6 |
| UTR Pro Tennis Series Cancun | 2021/03/31 17:00 | Jose Antonio Rodriguez Rodriguez v Drew Van Orderlain | 6-2,5-1 |
| UTR Pro Tennis Series Cancun | 2021/03/30 15:00 | Felix Corwin v Drew Van Orderlain | 6-2,6-1 |
| UTR Pro Tennis Series Florida | 2021/01/15 18:15 | Drew Van Orderlain v Fletcher Scott | 2-6,2-6 |
| UTR Pro Tennis Series Florida | 2021/01/14 14:00 | Matthew Segura v Drew Van Orderlain | 4-6,6-4,5-3 |
| UTR Pro Tennis Series Florida | 2021/01/11 18:30 | Nick Chappell v Drew Van Orderlain | 6-1,7-5 |
| UTR Pro Tennis Series Florida | 2021/01/10 16:30 | Anze Arh v Drew Van Orderlain | 6-1,3-6,0-3 |