Stadium: Court 2 Round: 44 Ground: Hardcourt outdoor
| ITF - M15 Monastir | 2021/08/01 09:00 | Joshua Sheehy v Gregg, Perry | 6-4,7-5 |
| ITF M15 Cancun | 2021/12/13 18:00 | Gregg, Perry v Kevin Gonzalez | 6-3,7-5 |
| ITF M15 Cancun | 2021/12/12 15:00 | Gregg, Perry v Lucca Pinto | 6-3,6-4 |
| ITF M15 Cancun | 2021/12/06 14:00 | Juan Sebastian Osorio v Gregg, Perry | 3-6,7-6,10-8 |
| ITF M15 Cancun | 2021/12/05 14:00 | Rico Arias, Nicolas Esteban v Gregg, Perry | 3-6,4-6 |
| ITF M15 Cancun | 2021/12/04 14:00 | Gregg, Perry v Isaiah Strode | 4-6,6-3,7-10 |
| ITF M15 Cancun | 2021/12/02 16:00 | Makoto Ochi v Gregg, Perry | 3-6,4-6 |
| ITF M15 Cancun | 2021/11/30 16:00 | Wojcik, Jakub v Gregg, Perry | 3-6,4-6 |
| ITF M15 Cancun | 2021/11/29 14:00 | Versier, Vivien v Gregg, Perry | 6-4,3-6,3-10 |
| ITF M15 Cancun | 2021/12/13 18:00 | Marcelo Marino Hidalgo v Joshua Sheehy | 2-6,2-6 |
| ITF M15 Cancun | 2021/12/06 14:00 | Joshua Sheehy v Kiranpal Pannu | 4-6,4-6 |
| ITF M15 Cancun | 2021/12/04 14:00 | Nam Hoang Ly v Joshua Sheehy | 6-2,6-2 |
| ITF M15 Cancun | 2021/12/02 17:00 | Joshua Sheehy v Luis Britto | 6-2,6-0 |
| ITF M15 Cancun | 2021/11/30 16:00 | Ren Nakamura v Joshua Sheehy | 6-7,0-6 |
| ITF M15 Cancun | 2021/11/29 14:00 | Gal Emersic Potocnik v Joshua Sheehy | 4-6,6-7 |
| ITF M15 Cancun | 2021/11/28 14:00 | Dynka, Tom v Joshua Sheehy | 2-6,2-6 |
| ITF M15 Cancun | 2021/11/23 14:00 | Joshua Sheehy v Doria, Luciano | 3-6,6-4,7-10 |