Estadio: Stadium Round: 26 Ground: Hardcourt outdoor
| ITF M15 Santo Domingo | 2019/11/27 16:45 | Matthew Mendez v José Olivares | 3-6,1-6 |
| ITF M25 Orlando | 2019/11/12 19:25 | José Olivares v Pedro Sakamoto | 2-6,3-6 |
| ITF M25 Naples | 2019/10/30 14:00 | José Olivares v Jesse Witten | 5-7,6-7 |
| Challenger de Santo Domingo | 2019/10/08 02:00 | José Olivares v Thiago Seyboth Wild | 3-6,4-6 |
| ITF M15 Santa Tecla | 2019/10/04 22:05 | Ricardo Rodriguez-Pace v José Olivares | 6-2,7-6 |
| ITF M15 Santa Tecla | 2019/10/04 15:00 | José Olivares v Alex Blumenberg | 6-3,7-5 |
| ITF M15 Santa Tecla | 2019/10/02 16:30 | José Olivares v Yeudy Villar | 6-1,6-3 |
| ITF M15 Santa Tecla | 2019/10/01 17:00 | José Olivares v Felipe Santamaria | 7-6,6-3 |
| ITF M15 Santo Domingo | 2019/11/27 17:00 | Pedro Iamachkine v Gage Brymer | 3-6,4-6 |
| ITF M15 Cancun | 2019/11/22 14:00 | Matheus P De Almeida v Gage Brymer | 6-4,7-6 |
| ITF M15 Cancun | 2019/11/21 17:10 | Karlo Cubelic v Gage Brymer | 2-6,2-6 |
| ITF M15 Cancun | 2019/11/20 19:45 | David Volfson v Gage Brymer | 6-3,5-7,3-6 |
| Challenger de Houston | 2019/11/11 21:10 | Gage Brymer v Collin Altamirano | 2-6,6-7 |
| ITF M25 Malibú | 2019/11/06 21:25 | Gage Brymer v Ruan Roelofse | 4-6,4-6 |
| Challenger Playford 2 | 2019/10/29 00:45 | Akira Santillan v Gage Brymer | 6-1,6-3 |
| Challenger Playford 2 | 2019/10/28 03:50 | Bradley Mousley v Gage Brymer | 2-6,1-6 |