Jim Courier defeated Michael Chang 7-5 3-6 7-5 in the Orlando final on clay. The upset overturned the form book — Michael Chang came in defending the title. Jim Courier extended 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) |
| 1998-07-20 | Washington | QF | hard | Michael Chang | 6-3 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 (96 vs 200). ATP, WTA & Challenger.