Ivan Rodrigo defeated Oscar Martinez Dieguez 6-4 6-3 in the Spain 3 Masters 2 round of 16 on clay. The upset overturned the form book — Oscar Martinez Dieguez came in leading the head-to-head 2–1. Ivan Rodrigo narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-07 | Spain 5 Masters 3 | R16 | clay | Oscar Martinez Dieguez | 6-2 6-7 6-3 |
| 1997-10-17 | Spain 9 Masters 1 | R32 | clay | Ivan Rodrigo | 3-6 7-5 6-3 |
| 1997-07-04 | Spain 6 Masters 1 | SF | clay | Oscar Martinez Dieguez | 1-6 7-5 6-2 |