Michael Chang defeated Jim Courier 6-3 6-4 in the Washington quarter-final on hard. The upset overturned the form book — Jim Courier came in leading the head-to-head 2–0. Michael Chang claimed a first win over Jim Courier in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-15 | Memphis | R32 | hard | Jim Courier | 6-4 7-6(8) |
| 1998-04-20 | Orlando | F | clay | Jim Courier | 7-5 3-6 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 (200 vs 96). ATP, WTA & Challenger.