Round: 44 Ground: Clay
| 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 Houston | 2019/09/20 00:00 | Ricardo Rodriguez-Pace v Oliver Crawford | 6-3,6-7,6-7 |
| ITF M25 Orlando | 2019/11/11 15:00 | JanMagnus Johnson v Alejandro Moro Canas | 3-6,4-6 |
| ITF M25 Naples | 2019/10/28 21:00 | JanMagnus Johnson v Daniel Labrador | 2-6,6-7 |
| ITF M25 Naples | 2019/10/27 14:00 | JanMagnus Johnson v Emmett Ward | 6-1,6-2 |
| ITF M25 Memphis | 2019/08/14 16:30 | Alexander Sarkissian v JanMagnus Johnson | 6-2,6-3 |
| ITF M25 Edwardsville | 2019/08/07 22:50 | JanMagnus Johnson v Liam Caruana | 0-6,1-6 |
| ITF M25 Edwardsville | 2019/08/06 14:00 | JanMagnus Johnson v Bradley Frye | 6-3,6-4 |
| ITF M25 Edwardsville | 2019/08/05 14:00 | Adrian Chamdani v JanMagnus Johnson | 7-5,3-6,4-10 |
| ITF M25 Decatur | 2019/07/29 18:00 | Ishaan Ravichander v JanMagnus Johnson | 6-3,6-3 |