Stadium: Court 7 Round: 26 Ground: Hardcourt outdoor
| UTR Pro Tennis Series Cancun | 2020/11/22 16:30 | Oliver Crawford v Gage Brymer | 6-3,6-2 |
| ITF - Santo Domingo M25 | 2022/03/02 14:45 | Victor Lilov v Gage Brymer | 4-6,2-6 |
| ITF - Cancun M25 | 2022/02/15 17:20 | Gage Brymer v Jaimee Floyd Angele | 7-6,2-6,3-6 |
| ITF - Cancun M25 | 2022/02/11 14:30 | Gage Brymer v JC Aragone | 1-6,3-6 |
| ITF - Cancun M25 | 2022/02/08 14:00 | Gage Brymer v Juan Sebastian Gomez | 3-6,6-3,6-3 |
| ITF - Cancun M15 | 2022/02/04 20:15 | Brandon Holt v Gage Brymer | 6-3,6-1 |
| ITF - Cancun M15 | 2022/02/02 17:10 | Nikolay Sysoev v Gage Brymer | 5-7,4-6 |
| ITF - Cancun M15 | 2022/01/27 15:00 | Gage Brymer v Luis Patino | 4-6,2-6 |
| ITF - Cancun M15 | 2022/01/25 16:00 | Gage Brymer v Sandro Kopp | 6-4,3-6,7-5 |
| ITF - Santo Domingo M25 | 2022/03/01 19:00 | Enmanuel Munoz v Oliver Crawford | 4-6,0-6 |
| ITF - Santo Domingo M25 | 2022/02/23 18:00 | Oliver Crawford v Christian Harrison | 4-6,7-6,4-6 |
| ITF - Cancun M25 | 2022/02/17 15:00 | Keegan Smith v Oliver Crawford | 6-3,6-2 |
| ITF - Cancun M25 | 2022/02/16 15:00 | JC Aragone v Oliver Crawford | 4-6,4-6 |
| ITF - Cancun M25 | 2022/02/09 22:15 | Keegan Smith v Oliver Crawford | 3-6,7-5,6-3 |
| ITF - Weston M25 | 2022/01/27 18:50 | Oliver Crawford v Leandro Riedi | 4-6,2-6 |
| ITF - Weston M25 | 2022/01/26 14:00 | Oliver Crawford v Ethan Quinn | 6-3,6-3 |
| Challenger Antalya | 2021/12/02 07:00 | Oliver Crawford v Ramkumar Ramanathan | 5-7,4-6 |