Stadium: Court 2N Round: 25 Ground: Hardcourt outdoor
| 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 Monastir | 2021/07/25 12:00 | Ethan Terblanche v Perry Gregg | 1-6,2-6 |
| ITF M15 Monastir | 2021/07/20 08:30 | Santiago Rodriguez Taverna v Perry Gregg | 6-4,1-6,6-3 |
| ITF M15 Monastir | 2021/07/14 12:50 | Perry Gregg v Jake Van Emburgh | 7-6,6-7,4-6 |
| ITF M15 Monastir | 2021/07/12 14:30 | Alexandros Skorilas v Perry Gregg | 0-6,3-6 |
| ITF M15 Monastir | 2021/07/12 09:00 | Valentino De Pellegrin v Perry Gregg | 1-6,6-3,10-12 |
| ITF M25 Champaign | 2021/07/28 19:10 | Martin Damm v Jumpei Yamasaki | 6-7,6-7 |
| ITF M15 Edwardsville | 2021/07/21 22:10 | Martin Damm v Cannon Kingsley | 3-6,4-6 |
| ITF M25 Klosters | 2021/06/22 08:30 | Martin Damm v Henry V-D Schulenburg | 4-6,4-6 |
| ITF M15 Skopje | 2021/06/11 10:30 | Martin Damm v Simone Roncalli | 3-6,0-6 |
| ITF M15 Skopje | 2021/06/10 10:30 | Martin Damm v Stefan Micov | 6-4,3-6,6-2 |
| ITF M15 Skopje | 2021/06/09 10:50 | Marko Tepavac v Martin Damm | 5-7,3-6 |
| ITF M15 Skopje | 2021/06/03 08:00 | Alexander Weis v Martin Damm | 6-3,6-2 |
| ITF M15 Skopje | 2021/06/02 11:45 | Tomislav Jotovski v Martin Damm | 6-7,4-6 |