Jim Courier defeated Michael Chang 7-6 7-6 7-5 in the US Open quarter-final on hard. The upset overturned the form book — Michael Chang came in leading the head-to-head 5–4, defending last year's round of 16, but Jim Courier had been the form player, winning 4 of their last 9 on hard. Jim Courier 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 |
| 1995-04-17 | Hong Kong | SF | hard | Michael Chang | 6-4 6-2 |
| 1995-02-06 | San Jose | SF | hard | Michael Chang | 4-6 7-6(5) 6-4 |
| 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 (147 vs 200). 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