Stadium: Court 3 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2021/06/13 09:00 | Perry Gregg v Nicolas Bruna | 6-3,2-6,19-17 |
| ITF M15 Monastir | 2021/06/01 12:50 | Lukas Neumayer v Perry Gregg | 6-4,6-2 |
| ITF M15 Monastir | 2021/05/24 13:30 | Yuta Kikuchi v Perry Gregg | 6-3,6-1 |
| ITF M15 Monastir | 2021/05/23 13:00 | Luc Koenig v Perry Gregg | 3-6,3-6 |
| ITF M15 Monastir | 2021/05/17 13:30 | Yuta Kikuchi v Perry Gregg | 6-2,6-3 |
| ITF M15 Monastir | 2021/05/17 09:00 | Riccardo Chessari v Perry Gregg | 3-6,4-6 |
| Challenger Tallahassee | 2021/04/18 22:40 | Agustin Velotti v Perry Gregg | 6-4,6-3 |
| Challenger Cleveland | 2021/03/14 18:10 | Perry Gregg v Alexis Galarneau | 1-6,2-6 |
| ITF M15 Monastir | 2021/06/13 09:00 | Valentino De Pellegrin v Siddhant Banthia | 6-3,4-6,11-9 |
| ITF M15 Monastir | 2021/06/06 09:00 | Ezequiel Simonit v Valentino De Pellegrin | 6-1,6-3 |
| ITF M15 Monastir | 2021/05/31 09:00 | Ajeet Rai v Valentino De Pellegrin | 6-1,6-3 |
| ITF M15 Cordoba | 2021/04/04 12:30 | Luciano Carraro v Valentino De Pellegrin | 6-4,6-0 |