Stadium: Court 8 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2021/05/16 11:00 | Mhamed Affes v Riccardo Chessari | 4-6,1-6 |
| ITF M15 Monastir | 2021/05/10 08:00 | Riccardo Chessari v Uisung Park | 1-6,2-6 |
| ITF M15 Monastir | 2021/05/09 08:00 | Giovanni Agostinetto v Riccardo Chessari | 6-7,0-6 |
| ITF M15 Monastir | 2021/05/02 10:30 | Riccardo Chessari v Omni Kumar | 1-6,2-6 |
| ITF Poland F8 Qual | 2017/07/31 09:30 | Riccardo Chessari v Oleksander Kyrychenko | 5-7,2-4 |
| ITF Egypt F16 | 2016/07/16 19:00 | Riccardo Chessari v Anshuman Gulia | 6-1,6-0 |
| ITF Egypt F15 | 2016/07/10 16:00 | Flavio De Lucia v Riccardo Chessari | 3-6,6-3,6-7 |
| 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 | 2021/01/07 11:50 | Kaichi Uchida v Perry Gregg | 6-4,6-1 |
| ITF M15 Monastir | 2021/01/06 13:15 | Brandon Stringfellow v Perry Gregg | 1-6,4-6 |
| ITF M15 Monastir | 2021/01/04 09:30 | Perry Gregg v Edouard Villoslada | 3-6,7-6,10-5 |
| ITF M15 Monastir | 2020/12/31 11:35 | Perry Gregg v Skander Mansouri | 6-7,3-6 |
| ITF M15 Monastir | 2020/12/30 08:00 | Luca Sanchez v Perry Gregg | 6-3,4-6,6-7 |
| ITF M15 Monastir | 2020/12/21 14:00 | Clement Deleersnyder v Perry Gregg | 7-6,7-6 |