Stadium: Court 2 Round: 26 Ground: Clay
| 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 Houston | 2019/09/20 00:00 | Ricardo Rodriguez-Pace v Oliver Crawford | 6-3,6-7,6-7 |
| ITF M25 Houston | 2019/09/18 23:45 | Sumit Sarkar v Oliver Crawford | 3-6,5-7 |
| Challenger Lexington | 2019/07/30 23:40 | Enzo Wallart v Oliver Crawford | 6-4,6-3 |
| ITF M25 Naples | 2019/10/30 14:50 | Cristian Rodriguez v Alejandro Gomez | 6-3,3-6,6-3 |
| ITF M15 Cancun | 2019/10/26 14:15 | Cristian Rodriguez v Mariano Kestelboim | 6-3,7-6 |
| ITF M15 Cancun | 2019/10/25 14:15 | Cristian Rodriguez v Luca Keist | 7-5,6-3 |
| ITF M15 Cancun | 2019/10/24 15:00 | Cristian Rodriguez v Kiranpal Pannu | 6-2,6-3 |
| ITF M15 Cancun | 2019/10/23 20:15 | Cristian Rodriguez v Siddhant Banthia | 6-3,6-4 |
| ITF M15 Cancun | 2019/10/20 14:15 | Cristian Rodriguez v Tigre Hank | 4-6,7-6,3-6 |
| ITF M15 Cancun | 2019/10/19 14:15 | Jorge Panta v Cristian Rodriguez | 3-6,1-6 |
| ITF M15 Cancun | 2019/10/18 14:15 | Gerardo L Villasenor v Cristian Rodriguez | 6-7,5-7 |