Pete Sampras advanced when Greg Rusedski retired 3-6 5-0 in the San Jose final. Pete Sampras extended the head-to-head to 6–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-08-26 | US Open | R32 | hard | Pete Sampras | 7-6(4) 4-6 7-6(3) 3-6 6-4 |
| 2000-03-20 | Miami Masters | R16 | hard | Pete Sampras | 6-3 6-3 |
| 2000-03-06 | Scottsdale | R32 | hard | Pete Sampras | 6-3 6-4 |
| 1998-11-02 | Paris Masters | F | hard | Greg Rusedski | 6-4 7-6(4) 6-3 |
| 1997-11-10 | Tour Finals | RR | hard | Pete Sampras | 6-4 7-5 |
| 1997-09-23 | Grand Slam Cup | SF | carpet | Pete Sampras | 3-6 7-6 7-6 6-2 |
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 200). ATP, WTA & Challenger.