Miguel Angel Lopez Jaen defeated Roberto Menendez 6-1 6-1 in the Spain 1 4 round of 32 on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 5–0. Miguel Angel Lopez Jaen claimed a first win over Roberto Menendez in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-05 | Spain 3 3 | SF | clay | Roberto Menendez | 6-4 6-2 |
| 2002-03-04 | Spain 3 1 | R32 | clay | Roberto Menendez | 6-3 6-4 |
| 2001-02-05 | Spain 2 1 | R32 | clay | Roberto Menendez | 6-2 3-6 6-3 |
| 2000-09-04 | Spain F9 | SF | clay | Roberto Menendez | 4-2 4-2 4-2 |
| 2000-07-24 | Spain F3 | R16 | clay | Roberto Menendez | 6-4 7-6(3) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.