Thomas Enqvist defeated Jim Courier 6-7 6-3 6-4 in the Miami 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 64. Thomas Enqvist 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 | R16 | hard | Jim Courier | 6-7(3) 7-6(4) 7-5 |
| 1997-07-21 | Los Angeles | F | hard | Jim Courier | 6-4 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 (200 vs 8). ATP, WTA & Challenger.