John Van Lottum defeated Jim Courier 6-4 7-6 in the San Jose round of 32 on hard. The upset overturned the form book — Jim Courier came in leading the head-to-head 1–0. John Van Lottum claimed a first win over Jim Courier in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-15 | Memphis | SF | hard | Jim Courier | 7-6(5) 4-6 6-4 |
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 (109 vs 57). ATP, WTA & Challenger.