Paul Oosterbaan defeated Alejandro Gomez 6-4 6-1 in the M25 Palm Coast 1 round of 32 on clay. The upset overturned the form book — Alejandro Gomez came in leading the head-to-head 2–0, but Paul Oosterbaan had been the form player, winning 6 of their last 9 on clay. Paul Oosterbaan claimed a first win over Alejandro Gomez in three meetings, narrowing 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 |
| 2019-05-09 | M25 Pensacola 1 | R16 | clay | Alejandro Gomez | 6-2 7-6(5) |