Albert Montanes defeated Roberto Menendez 6-0 6-3 in the Spain 5 Masters 1 qualifying round on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 2–0. Albert Montanes claimed a first win over Roberto Menendez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-07 | Spain 5 Masters 4 | R32 | clay | Roberto Menendez | 7-5 6-1 |
| 1999-04-09 | Spain 4 Masters 1 | R16 | clay | Roberto Menendez | 7-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.