Stadium: Court 2 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2021/08/01 09:00 | Joshua Sheehy v Perry Gregg | 6-4,7-5 |
| ITF M15 Cancun | 2021/11/24 14:00 | Chad Kissell v Perry Gregg | 6-3,7-6 |
| ITF M15 Cancun | 2021/09/27 14:30 | Perry Gregg v Luis Britto | 6-3,5-7,4-10 |
| ITF M15 Cancun | 2021/09/23 14:00 | Perry Gregg v Gerardo L Villasenor | 6-7,3-6 |
| ITF M15 Cancun | 2021/09/22 17:30 | Julian Cundom v Perry Gregg | 1-6,2-6 |
| ITF M15 Champaign | 2021/09/15 20:45 | Perry Gregg v Martin Damm | 5-7,0-6 |
| ITF M25 Champaign | 2021/09/14 17:00 | Perry Gregg v Osgar O'Hoisin | 6-2,6-3 |
| ITF M25 Champaign | 2021/09/13 17:00 | Perry Gregg v Parth Aggarwal | 6-2,5-7,10-2 |
| ITF M15 Monastir | 2021/08/01 09:00 | Joshua Sheehy v Perry Gregg | 6-4,7-5 |
| ITF M15 Cancun | 2021/11/23 14:00 | Matic Spec v Joshua Sheehy | 6-3,6-2 |
| ITF M15 Cancun | 2021/11/23 14:00 | Joshua Sheehy v Luciano Doria | 3-6,6-4,7-10 |
| ITF M15 East Lansing | 2021/11/16 16:00 | Joshua Sheehy v Alex Knaff | 3-6,2-6 |
| ITF M25 Calabasas | 2021/10/27 17:00 | Felix Corwin v Joshua Sheehy | 1-6,6-0,6-2 |
| ITF M25 Calabasas | 2021/10/26 20:00 | Joshua Sheehy v Miles Jones | 6-3,6-3 |
| ITF M15 Ithaca | 2021/10/05 13:00 | Joshua Sheehy v Sebastian Dominko | 4-6,6-7 |
| ITF M15 Cancun | 2021/09/30 14:30 | Joshua Sheehy v Emil Reinberg | 2-6,6-4,3-6 |
| ITF M15 Cancun | 2021/09/29 17:55 | Joshua Sheehy v Joao Victor C Loureiro | 7-6,4-6,6-4 |