Roberto Menendez defeated Albert Montanes 7-5 6-1 in the Spain 5 Masters 4 round of 32 on clay. Roberto Menendez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-07 | Spain 5 Masters 1 | QF | clay | Albert Montanes | 6-0 6-3 |
| 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.