Carlos Moya defeated Jim Courier 7-6 6-4 in the Indian Wells Masters round of 32 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 16. Carlos Moya 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 | R32 | hard | Jim Courier | 6-2 6-1 |
| 1999-06-21 | Wimbledon | R64 | grass | Jim Courier | 6-3 3-6 7-6(1) 3-6 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 (200 vs 57). ATP, WTA & Challenger.