Mario Munoz Bejarano defeated Roberto Menendez 6-3 7-6 in the Spain 3 2 round of 32 on clay. Mario Munoz Bejarano extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-15 | Spain 7 Masters 1 | QF | clay | Mario Munoz Bejarano | 6-2 6-4 |
| 1999-07-05 | Spain F1 | R32 | clay | Roberto Menendez | 5-7 6-4 6-4 |