Arnaud Di Pasquale defeated Alberto Berasategui 7-6 5-7 6-4 in the Monte Carlo Masters round of 64 on clay. The upset overturned the form book — Alberto Berasategui came in defending last year's semi-final, but Arnaud Di Pasquale had been the form player, winning 2 of their last 7 on clay. Arnaud Di Pasquale extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Palermo | F | clay | Arnaud Di Pasquale | 6-1 6-3 |
| 1999-04-12 | Barcelona | R64 | clay | Alberto Berasategui | 6-3 6-2 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (139 vs 57). ATP, WTA & Challenger.