Arnaud Di Pasquale defeated Jim Courier 7-5 4-6 7-6 in the Indian Wells Masters round of 64 on hard. The upset overturned the form book — Jim Courier came in leading the head-to-head 2–0, defending last year's round of 32. Arnaud Di Pasquale claimed a first win over Jim Courier in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Paris Masters | R64 | hard | Jim Courier | 7-6(5) 3-6 7-6(6) |
| 1999-10-18 | Lyon | R64 | clay | Jim Courier | 2-6 7-6(2) 7-5 |
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 (89 vs 8). ATP, WTA & Challenger.