Alejandro Gomez defeated Paul Oosterbaan 6-2 7-6 in the M25 Pensacola 1 round of 16 on clay. Alejandro Gomez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-28 | M15 Cancun 10 | R32 | hard | Alejandro Gomez | 6-2 4-6 6-3 |
| 2019-01-22 | M25 Palm Coast 1 | R32 | clay | Paul Oosterbaan | 6-4 6-1 |