Stadium: Court 2 Round: 25 Ground: Clay
| ITF M25 Pensacola | 2019/05/10 17:50 | Jose Olivares v Felix Corwin | 1-6,6-3,2-6 |
| ITF M25 Pensacola | 2019/05/09 15:00 | Andrew Watson v Jose Olivares | 7-6,4-6,1-6 |
| ITF M25 Pensacola | 2019/05/08 14:00 | Jose Olivares v Sergey Belov | 6-4,2-6,6-4 |
| ITF M25 Vero Beach | 2019/05/02 14:00 | Pedro Sakamoto v Jose Olivares | 7-5,6-2 |
| ITF M25 Vero Beach | 2019/05/01 16:00 | Jose Olivares v Baker Newman | 2-6,6-1,6-2 |
| ITF M15 Orange Park | 2019/04/20 16:00 | Dmitry Popko v Jose Olivares | 6-2,6-1 |
| ITF M15 Orange Park | 2019/04/19 13:15 | Ricardo Rodriguez-Pace v Jose Olivares | 4-6,3-6 |
| ITF M15 Orange Park | 2019/04/18 15:00 | Yeudy Villar v Jose Olivares | 6-7,0-6 |
| ITF M15 Naples | 2019/01/16 17:30 | Nicolas Alvarez v Jesse Witten | 6-3,6-3 |
| ITF M15 Naples | 2019/01/15 15:30 | Facundo Mena v Jesse Witten | 6-3,6-2 |
| ITF M15 Naples | 2019/01/14 17:00 | Jesse Witten v Lucas Renard | 6-3,6-2 |
| Challenger Lexington Qual | 2018/07/29 13:00 | Mikael Torpegaard v Jesse Witten | 6-3,2-6,7-5 |
| Challenger Lexington Qual | 2018/07/28 18:05 | Jesse Witten v N. Vijay Sundar Prashanth | 6-4,6-4 |
| Challenger Lexington Qual | 2018/07/28 17:00 | Jesse Witten v N. V. Sundar S-Prashanth | 6-4,5-4 |
| ITF USA F5 | 2018/01/23 17:50 | Gonzalo Escobar v Jesse Witten | 6-2,6-2 |
| ITF USA F3 | 2018/01/12 22:40 | Javier Marti v Jesse Witten | 6-2,6-4 |