| UTR Pro Tennis Series Florida | 2021/01/23 14:00 | Charles Sullivan v Giulio Perego | 4-6,2-6 |
| UTR Pro Tennis Series Florida | 2021/01/22 16:00 | Jordi Arconada v Charles Sullivan | 4-6,2-6 |
| UTR Pro Tennis Series Florida | 2021/01/21 14:00 | Joshua Sheehy v Charles Sullivan | 3-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/01/20 14:00 | David Volfson v Charles Sullivan | 7-6,4-6,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/18 15:30 | Matija Pecotic v Charles Sullivan | 6-2,6-2 |
| UTR Pro Tennis Series Florida | 2021/01/16 14:00 | Charles Sullivan v Fletcher Scott | 6-4,6-7,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/14 20:13 | Charles Sullivan v Gabrielius Guzauskas | 7-5,3-0 |
| UTR Pro Tennis Series Florida | 2021/01/13 16:00 | Harris Walker v Charles Sullivan | 6-4,5-4 |