Stadium: Court 3 Round: 44 Ground: Clay
| ITF - M25 Naples | 2019/11/17 14:00 | Oliver Crawford v JanMagnus Johnson | 7-6,6-1 |
| Challenger - Houston | 2019/11/11 19:05 | Govind Nanda v Oliver Crawford | 6-4,6-3 |
| ITF - M25 Naples | 2019/10/31 16:05 | Oliver Crawford v Cristian Rodriguez | 2-6,3-6 |
| ITF - M25 Naples | 2019/10/29 15:40 | Oliver Crawford v Daniel Labrador | 6-1,6-1 |
| ITF - M25 Naples | 2019/10/28 14:00 | Oliver Crawford v Thomas Bosancic | 6-3,6-2 |
| ITF - M25 Naples | 2019/10/27 14:00 | Oliver Crawford v Patrick Daciek | 6-2,6-0 |
| Challenger - Tiburon | 2019/09/24 17:00 | Edan Leshem v Oliver Crawford | 6-7,6-4,6-4 |
| ITF M25 Houston | 2019/09/21 01:00 | Oliver Crawford v Hugo Gaston | 3-6,2-6 |
| ITF - M25 Naples | 2019/11/17 14:00 | Aidan Mayo v Michel-Alexandre Fortin | 6-2,6-2 |
| ITF M25 Orlando | 2019/11/12 15:00 | Gonzalo Lama v Aidan Mayo | 7-5,6-2 |
| ITF M25 Orlando | 2019/11/11 15:00 | Aidan Mayo v Patrick Daciek | 6-3,6-2 |
| ITF M15 Claremont | 2019/02/06 17:00 | Aidan Mayo v Julian Bradley | 4-6,1-6 |
| ITF M15 Claremont | 2019/02/05 20:30 | Conor Berg v Aidan Mayo | 6-7,3-6 |