Marc Marco Ripoll defeated Roberto Menendez 2-6 6-4 6-0 in the Spain 1 1 round of 32 on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 4–0. Marc Marco Ripoll claimed a first win over Roberto Menendez in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-04-09 | Spain 4 2 | R32 | clay | Roberto Menendez | 6-4 5-7 6-4 |
| 2000-07-17 | Spain F2 | R32 | clay | Roberto Menendez | 6-4 6-4 |
| 2000-04-07 | Spain 4 4 | R16 | clay | Roberto Menendez | 6-1 6-2 |
| 1999-10-15 | Spain 7 Masters 1 | R16 | clay | Roberto Menendez | 7-5 3-6 6-1 |