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 4–0, defending last year's round of 64. Thomas Enqvist claimed a first win over Jim Courier in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Paris Masters | R16 | hard | Jim Courier | 6-7 7-6 7-5 |
| 1997-07-21 | Los Angeles | F | hard | Jim Courier | 6-4 6-4 |
| 1995-01-02 | Adelaide | QF | hard | Jim Courier | 6-2 6-4 |
| 1992-01-13 | Australian Open | R64 | hard | Jim Courier | 2-6 6-3 6-1 6-4 |
Averages over each player's completed matches in the selected window (200 vs 8). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About