Stadium: Court 2 Round: 25 Ground: Clay
| 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 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2019/09/18 18:35 | Guido Ivan Justo v Olivares, Jose | 6-0,7-5 |
| ITF M15 Cancun | 2019/08/30 16:30 | Federico Zeballos v Olivares, Jose | 6-2,6-4 |
| ITF M15 Cancun | 2019/08/29 16:20 | Naoki Nakagawa v Olivares, Jose | 7-6,3-6,4-6 |
| ITF - M25 Naples | 2019/10/29 14:00 | Witten, Jesse v Melnic, Vladislav | 6-4,4-6,10-3 |
| ITF - M25 Naples | 2019/10/28 14:00 | Leote Prata, Martim v Witten, Jesse | 4-6,7-5,10-12 |
| ITF - M25 Naples | 2019/10/27 14:00 | Alexander Bernard v Witten, Jesse | 4-6,2-6 |
| ITF M15 Cancun | 2019/09/23 16:00 | Witten, Jesse v Banzer, Rodrigo | 6-2,6-7,8-10 |
| ITF M15 Cancun | 2019/09/23 14:00 | Martinez, Esdras v Witten, Jesse | 2-6,1-6 |
| ITF M15 Cancun | 2019/09/22 18:30 | Fortin, Michel-Alexandre v Witten, Jesse | 3-6,1-6 |
| ITF M15 Naples | 2019/01/16 17:30 | Nicolas Alvarez v Witten, Jesse | 6-3,6-3 |
| ITF M15 Naples | 2019/01/15 15:30 | Facundo Mena v Witten, Jesse | 6-3,6-2 |