Stadium: Stadium Round: 27 Ground: Hardcourt outdoor
| ITF M15 Santo Domingo | 2020/12/03 13:30 | Felix Corwin v Oliver Crawford | 5-7,3-6 |
| ITF M15 Santo Domingo | 2020/12/01 14:30 | Dhruva Mulye v Oliver Crawford | 0-6,0-6 |
| UTR Pro Tennis Series Cancun | 2020/11/22 16:30 | Oliver Crawford v Gage Brymer | 6-3,6-2 |
| 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 M15 Santo Domingo | 2020/12/03 17:20 | Zane Khan v Nick Hardt | 6-3,6-2 |
| ITF M15 Santo Domingo | 2020/12/02 13:30 | Nicolas Jarry v Zane Khan | 4-6,4-6 |
| ITF M15 Santo Domingo | 2020/12/01 13:30 | Zane Khan v Charles Broom | 6-3,7-6 |
| ITF M15 Santo Domingo | 2020/11/30 13:30 | Zane Khan v Toby D. Boyer | 6-4,6-1 |
| Challenger Orlando | 2020/11/15 15:00 | Zachary Svajda v Zane Khan | 7-6,6-4 |
| Challenger Orlando | 2020/11/14 18:00 | Zane Khan v Nicolas Mejia | 6-1,6-2 |
| Challenger Cary | 2020/11/07 15:00 | Thomaz Bellucci v Zane Khan | 6-2,6-3 |
| ITF M25 Fayetteville | 2020/11/03 16:00 | Zane Khan v Trent Bryde | 5-7,5-7 |