Stadium: Court 24 Round: 26 Ground: Clay
| ITF M25 Pensacola | 2019/05/08 15:35 | Jordi Arconada v Andrew Watson | 3-6,6-3,4-6 |
| ITF M25 Vero Beach | 2019/05/02 14:00 | Andrew Watson v Paul Oosterbaan | 4-6,3-6 |
| ITF M25 Vero Beach | 2019/04/30 16:00 | Bastian Malla v Andrew Watson | 6-7,5-7 |
| ITF M15 Cancun | 2019/04/18 18:55 | Andrew Watson v Adam El Mihdawy | 4-6,0-6 |
| ITF M15 Cancun | 2019/04/16 14:00 | Andrew Watson v Eduardo Ribeiro | 7-5,6-3 |
| ITF M15 Cancun | 2019/03/28 14:00 | Juan Pablo Varillas v Andrew Watson | 3-6,7-6,6-2 |
| ITF M15 Cancun | 2019/03/27 16:30 | Gabriel Donev v Andrew Watson | 0-6,2-6 |
| ITF M15 Cancun | 2019/03/21 19:30 | Andrew Watson v Emil Ruusuvuori | 1-6,4-6 |
| 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 Orange Park | 2019/04/17 14:00 | Jose Olivares v Harrison Adams | 6-4,6-1 |
| ITF M15 Sunrise | 2019/04/08 15:00 | Jose Olivares v Peter Bertran | 6-2,3-6,6-10 |