Michael Chang defeated Jim Courier 4-6 7-6 6-4 in the San Jose semi-final on hard. The upset overturned the form book — Jim Courier came in leading the head-to-head 5–4. Michael Chang narrowed the head-to-head to 5–5.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-15 | Memphis | R32 | hard | Jim Courier | 6-4 7-6 |
| 1998-07-20 | Washington | QF | hard | Michael Chang | 6-3 6-4 |
| 1998-04-20 | Orlando | F | clay | Jim Courier | 7-5 3-6 7-5 |
| 1995-08-28 | US Open | QF | hard | Jim Courier | 7-6(5) 7-6(3) 7-5 |
| 1995-04-17 | Hong Kong | SF | hard | Michael Chang | 6-4 6-2 |
| 1994-02-14 | Philadelphia | SF | hard | Michael Chang | 7-6(6) 6-2 |
| 1993-04-12 | Hong Kong | SF | hard | Jim Courier | 6-2 6-3 |
| 1992-04-13 | Hong Kong | F | hard | Jim Courier | 7-5 6-3 |
| 1991-12-09 | Grand Slam Cup | R16 | carpet | Michael Chang | 6-4 6-2 |
Averages over each player's completed matches in the selected window (200 vs 147). 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