Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Santo Domingo | 2020/12/06 13:55 | Oliver Crawford v Alex Rybakov | 6-3,6-1 |
| ITF M15 Santo Domingo | 2020/12/05 14:30 | Nick Chappell v Oliver Crawford | 5-7,6-0,4-6 |
| ITF M15 Santo Domingo | 2020/12/04 17:30 | Oliver Crawford v Zane Khan | 6-3,6-2 |
| 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 Cancún | 2020/11/22 16:30 | Oliver Crawford v Gage Brymer | 6-3,6-2 |
| UTR Pro Tennis Series Cancún | 2020/11/21 15:45 | Oliver Crawford v Nicolas Barrientos | 6-3,6-3 |
| UTR Pro Tennis Series Cancún | 2020/11/20 14:00 | Oliver Crawford v Manuel Sanchez | 6-2,6-4 |
| ITF M15 Santo Domingo | 2020/12/01 14:30 | Justin Roberts v Roy Smith | 4-6,2-6 |
| ITF M25 Fayetteville | 2020/11/03 17:30 | Justin Roberts v Blaise Bicknell | 1-6,4-6 |
| ITF M25 Fayetteville | 2020/11/02 17:30 | Justin Roberts v Ivailo Keremedchiev | 6-3,6-4 |
| ITF M25 Las Vegas | 2020/03/04 17:50 | Justin Roberts v Spencer Papa | 1-6,3-6 |
| ITF - M15 Cancún | 2020/02/18 18:00 | Gilbert S K Junior v Justin Roberts | 6-4,7-5 |
| ITF - M15 Cancún | 2020/02/15 14:00 | Justin Roberts v Maximiliano Estevez | 2-6,3-6 |
| ITF - M15 Cancún | 2020/02/14 14:00 | Justin Roberts v Joshua Ortlip | 6-2,7-6 |
| ITF - M15 Cancún | 2020/02/13 18:55 | Justin Roberts v Juan A H Serrano | 6-3,7-6 |