Ruben Ramirez Hidalgo defeated Roberto Menendez 4-6 7-5 6-0 in the Spain F3 round of 32 on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 2–0. Ruben Ramirez Hidalgo claimed a first win over Roberto Menendez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-15 | Spain 7 Masters 2 | R16 | clay | Roberto Menendez | 6-4 6-4 |
| 1999-05-07 | Spain 5 Masters 1 | R32 | clay | Roberto Menendez | 6-4 6-7 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.