Carlos Martinez Comet defeated Kentaro Masuda 6-2 3-6 6-1 in the Spain 5 Masters 3 round of 32 on clay. The upset overturned the form book — Kentaro Masuda came in leading the head-to-head 1–0. Carlos Martinez Comet claimed a first win over Kentaro Masuda in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-06 | Spain F9 | R16 | clay | Kentaro Masuda | 4-6 6-4 6-1 |