Stadium: Court 1 Round: 54 Ground: Hardcourt outdoor
| ITF M15 South Bend | 2023/06/22 16:55 | Perry Gregg v James Tracy | 3-6,6-4,5-7 |
| ITF M15 South Bend | 2023/06/21 18:40 | Perry Gregg v Fabien Salle | 6-4,6-4 |
| ITF M15 San Diego | 2023/06/13 17:30 | Warren Wood v Perry Gregg | 6-3,7-5 |
| ITF M15 San Diego | 2023/06/05 17:00 | Piotr Galus v Perry Gregg | 5-7,7-6,10-6 |
| ITF M25 Malibu | 2023/01/03 21:20 | Rudy Quan v Perry Gregg | 7-5,0-6,10-1 |
| ITF M25 Malibu | 2023/01/02 17:00 | Elijah Strode v Perry Gregg | 6-7,6-7 |
| ITF M15 East Lansing | 2022/11/17 20:00 | Perry Gregg v Mitchell Harper | 2-6,1-6 |
| UTR Pro Tennis Series Indiana | 2022/09/04 12:30 | Perry Gregg v Alex Kuperstein | 3-6,6-2,7-6 |
| ITF M15 South Bend | 2023/06/21 17:05 | Adhithya Ganesan v Oliver Okonkwo | 6-0,6-3 |
| ITF M15 South Bend | 2023/06/20 15:00 | John Bernard v Oliver Okonkwo | 2-6,4-6 |
| ITF M15 South Bend | 2023/06/19 14:00 | Oliver Okonkwo v Sean Daryabeigi | 3-6,6-3,13-11 |
| UTR Pro London | 2023/05/20 10:16 | Luka Petrovic v Oliver Okonkwo | 6-4,6-4 |
| UTR Pro London | 2023/05/19 07:00 | Oliver Okonkwo v Ben Hudson | 6-3,5-4 |
| UTR Pro London | 2023/05/17 08:30 | Oliver Okonkwo v Kabeer Kapasi | 6-2,6-1 |
| UTR Pro London | 2023/05/16 11:30 | Oliver Okonkwo v Andres Gabriel Ciurletti | 0-6,6-2,6-5 |
| UTR Pro London | 2023/05/15 07:00 | Adam Jones v Oliver Okonkwo | 6-7,3-6 |