Stadium: Court 24 Round: 26 Ground: Clay
| ITF - M25 Pensacola | 2019/05/08 15:35 | Arconada, Jordi v Watson, Andrew | 3-6,6-3,4-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/02 14:00 | Watson, Andrew v C. Oosterbaan, Paul | 4-6,3-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/04/30 16:00 | Malla, Bastian v Watson, Andrew | 6-7,5-7 |
| ITF M15 Cancun | 2019/04/18 18:55 | Watson, Andrew v El Midhawy, Adam | 4-6,0-6 |
| ITF M15 Cancun | 2019/04/16 14:00 | Watson, Andrew v Eduardo Ribeiro | 7-5,6-3 |
| ITF M15 Cancun | 2019/03/28 14:00 | Juan Pablo Varillas v Watson, Andrew | 3-6,7-6,6-2 |
| ITF M15 Cancun | 2019/03/27 16:30 | Gabriel Donev v Watson, Andrew | 0-6,2-6 |
| ITF M15 Cancun | 2019/03/21 19:30 | Watson, Andrew v Emil Ruusuvuori | 1-6,4-6 |
| ITF - M25 Pensacola | 2019/05/08 14:00 | Olivares, Jose v Belov, Sergey | 6-4,2-6,6-4 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/02 14:00 | Pedro Sakamoto v Olivares, Jose | 7-5,6-2 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/01 16:00 | Olivares, Jose v Newman, Baker | 2-6,6-1,6-2 |
| ITF - M15 Orange Park | 2019/04/20 16:00 | Dmitry Popko v Olivares, Jose | 6-2,6-1 |
| ITF - M15 Orange Park | 2019/04/19 13:15 | Rodriguez-Pace, Ricardo v Olivares, Jose | 4-6,3-6 |
| ITF - M15 Orange Park | 2019/04/18 15:00 | Villar, Yeudy v Olivares, Jose | 6-7,0-6 |
| ITF - M15 Orange Park | 2019/04/17 14:00 | Olivares, Jose v Harrison Adams | 6-4,6-1 |
| ITF - M15 Sunrise | 2019/04/08 15:00 | Olivares, Jose v Peter Bertran | 6-2,3-6,6-10 |