Stadium: Stadium Round: 26 Ground: Hardcourt outdoor
| ITF M15 Santo Domingo | 2019/11/27 16:45 | Mendez, Matthew v Olivares, Jose | 3-6,1-6 |
| Orlando, Singles M-ITF-USA-38B | 2019/11/12 19:25 | Olivares, Jose v Pedro Sakamoto | 2-6,3-6 |
| ITF - M25 Naples | 2019/10/30 14:00 | Olivares, Jose v Witten, Jesse | 5-7,6-7 |
| Santo Domingo, Dominican Republic | 2019/10/08 02:00 | Olivares, Jose v Thiago Seyboth Wild | 3-6,4-6 |
| Santa Tecla, Singles M-ITF-ESA-01A | 2019/10/04 22:05 | Rodriguez-Pace, Ricardo v Olivares, Jose | 6-2,7-6 |
| Santa Tecla, Singles M-ITF-ESA-01A | 2019/10/04 15:00 | Olivares, Jose v Blumenberg, Alex | 6-3,7-5 |
| Santa Tecla, Singles M-ITF-ESA-01A | 2019/10/02 16:30 | Olivares, Jose v Villar, Yeudy | 6-1,6-3 |
| Santa Tecla, Singles M-ITF-ESA-01A | 2019/10/01 17:00 | Olivares, Jose v Santamaria, Felipe | 7-6,6-3 |
| ITF M15 Santo Domingo | 2019/11/27 17:00 | Iamachkine, Pedro v Brymer, Gage | 3-6,4-6 |
| ITF M15 Cancun | 2019/11/22 14:00 | Matheus P De Almeida v Brymer, Gage | 6-4,7-6 |
| ITF M15 Cancun | 2019/11/21 17:10 | Karlo Cubelic v Brymer, Gage | 2-6,2-6 |
| ITF M15 Cancun | 2019/11/20 19:45 | Volfson, David v Brymer, Gage | 6-3,5-7,3-6 |
| Houston, USA | 2019/11/11 21:10 | Brymer, Gage v Collin Altamirano | 2-6,6-7 |
| ITF M25 Malibu | 2019/11/06 21:25 | Brymer, Gage v Roelofse, Ruan | 4-6,4-6 |
| Playford City II, Australie | 2019/10/29 00:45 | Akira Santillan v Brymer, Gage | 6-1,6-3 |
| Playford City II, Australie | 2019/10/28 03:50 | Mousley, Bradley v Brymer, Gage | 2-6,1-6 |