Mark Philippoussis advanced past Pete Sampras via walkover in the San Jose semi-final. Mark Philippoussis narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Roland Garros | R128 | clay | Mark Philippoussis | 4-6 7-5 7-6(4) 4-6 8-6 |
| 1999-06-21 | Wimbledon | QF | grass | Pete Sampras | 4-6 2-1 RET |
| 1998-11-02 | Paris Masters | QF | hard | Pete Sampras | 6-3 6-3 |
| 1998-06-22 | Wimbledon | QF | grass | Pete Sampras | 7-6(5) 6-4 6-4 |
| 1997-09-19 | Davis Cup WG SF: USA vs AUS | RR | hard | Pete Sampras | 6-1 6-2 7-6(5) |
| 1997-05-19 | Dusseldorf | RR | clay | Mark Philippoussis | 4-6 6-4 0-1 RET |
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 191). ATP, WTA & Challenger.