Pete Sampras defeated Jim Courier 7-5 4-6 6-4 7-5 in the US Open semi-final on hard. The result followed the form book — Pete Sampras came in leading the head-to-head 9–3, defending last year's round of 16. Pete Sampras extended the head-to-head to 10–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-15 | Miami Masters | R64 | hard | Pete Sampras | 6-3 7-6 |
| 1997-05-12 | Rome Masters | R64 | clay | Jim Courier | 7-6 6-4 |
| 1996-05-27 | Roland Garros | QF | clay | Pete Sampras | 6-7(4) 4-6 6-4 6-4 6-4 |
| 1995-01-16 | Australian Open | QF | hard | Pete Sampras | 6-7(4) 6-7(3) 6-3 6-4 6-3 |
| 1994-05-23 | Roland Garros | QF | clay | Jim Courier | 6-4 5-7 6-4 6-4 |
| 1994-01-17 | Australian Open | SF | hard | Pete Sampras | 6-3 6-4 6-4 |
| 1993-06-21 | Wimbledon | F | grass | Pete Sampras | 7-6(3) 7-6(6) 3-6 6-3 |
| 1993-04-12 | Hong Kong | F | hard | Pete Sampras | 6-3 6-7(1) 7-6(2) |
| 1992-08-31 | US Open | SF | hard | Pete Sampras | 6-1 3-6 6-2 6-2 |
| 1992-08-17 | Indianapolis | F | hard | Pete Sampras | 6-4 6-4 |
| 1991-08-26 | US Open | QF | hard | Jim Courier | 6-2 7-6(4) 7-6(5) |
| 1991-08-12 | Indianapolis | SF | hard | Pete Sampras | 6-3 7-6(7) |
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