Estadio: Cancha 1 Round: 25
| Challenger de Santiago | 2021/10/12 15:25 | Oliver Crawford v Felipe Meligeni Rodrigues Alves | 6-7,3-6 |
| Challenger de Santiago | 2021/10/11 14:00 | Alexis Galarneau v Oliver Crawford | 3-6,4-6 |
| Challenger de Santiago - Clasificación | 2021/10/10 15:30 | Sebastian Santibanez v Oliver Crawford | 1-6,1-6 |
| Challenger de Santiago | 2021/10/05 16:40 | Goncalo Oliveira v Oliver Crawford | 6-4,6-2 |
| Challenger de Santiago | 2021/10/04 16:00 | Oliver Crawford v Jonathan Mridha | 7-5,6-3 |
| Challenger de Santiago | 2021/10/03 14:00 | Oliver Crawford v Daniel Antonio Nunez | 7-5,6-2 |
| ITF M25 Sierre | 2021/09/05 08:50 | Rinky Hijikata v Oliver Crawford | 7-6,6-1 |
| ITF M25 Sierre | 2021/09/04 10:20 | Patrick Kypson v Oliver Crawford | 3-6,4-6 |
| ITF M25 Guayaquil | 2021/10/25 17:05 | Luis Patino v Camilo Benavides Soto | 6-1,6-1 |