Oscar Martinez Dieguez defeated Albert Montanes 6-4 4-6 6-4 in the Spain F2 qualifying round on clay. The upset overturned the form book — Albert Montanes came in leading the head-to-head 1–0. Oscar Martinez Dieguez claimed a first win over Albert Montanes in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-07 | Spain 5 Masters 1 | SF | clay | Albert Montanes | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.