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