Kentaro Masuda defeated Manuel Sala 6-1 1-6 6-3 in the Spain F8 round of 16 on clay. The upset overturned the form book — Manuel Sala came in leading the head-to-head 2–0. Kentaro Masuda claimed a first win over Manuel Sala in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-07 | Spain 5 Masters 2 | R16 | clay | Manuel Sala | 6-2 6-0 |
| 1999-04-09 | Spain 4 Masters 2 | R32 | clay | Manuel Sala | 6-3 6-3 |