| UTR Pro Tennis Series Cancun | 2020/11/21 15:45 | Oliver Crawford v Nicolas Barrientos | 6-3,6-3 |
| UTR Pro Tennis Series Cancun | 2020/11/20 14:00 | Oliver Crawford v Manuel Sanchez | 6-2,6-4 |
| UTR Pro Tennis Series Cancun | 2020/11/19 17:00 | Oliver Crawford v Eric Samuelsson | 6-2,5-1 |
| UTR Pro Tennis Series Cancun | 2020/11/17 18:45 | Oliver Crawford v Alejandro H Franco | 3-1 |
| ITF M25 Naples | 2019/11/20 14:00 | Juan Pablo Ficovich v Oliver Crawford | 6-4,6-3 |
| ITF M25 Naples | 2019/11/19 13:55 | Oliver Crawford v Dragos Constantin Ignat | 6-4,7-5 |
| ITF M25 Naples | 2019/11/18 14:00 | Oliver Crawford v Aidan Mayo | 6-1,6-1 |
| ITF M25 Naples | 2019/11/17 14:00 | Oliver Crawford v JanMagnus Johnson | 7-6,6-1 |
| UTR Pro Tennis Series Cancun | 2020/11/21 15:45 | Maximiliano Estevez v Gage Brymer | 5-3 |
| UTR Pro Tennis Series Cancun | 2020/11/20 14:00 | Gage Brymer v Juan Ignacio Batalla | 6-3,5-3 |
| UTR Pro Tennis Series Cancun | 2020/11/17 17:00 | Gage Brymer v Tristan Meraut | 6-2,6-2 |
| UTR Pro Tennis Series Cancun | 2020/11/16 17:00 | Gage Brymer v Anze Arh | 6-0,5-1 |
| UTR Pro Tennis Series California | 2020/10/01 18:10 | Gage Brymer v Brandon Holt | 6-7,6-4,5-10 |
| UTR Pro Tennis Series California | 2020/10/01 16:15 | Nick Chappell v Gage Brymer | 6-3,3-6,3-10 |
| UTR Pro Tennis Series California | 2020/09/30 19:00 | Joshua Ortlip v Gage Brymer | 5-7,7-5,6-10 |
| UTR Pro Tennis Series California | 2020/09/29 15:00 | Martin Redlicki v Gage Brymer | 6-7,4-6 |