Pete Sampras defeated Mark Philippoussis 7-6 6-4 6-4 in the Wimbledon round of 64 on grass. The result followed the form book — Pete Sampras came in leading the head-to-head 6–3, defending the title. Pete Sampras extended the head-to-head to 7–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Roland Garros | R128 | clay | Mark Philippoussis | 4-6 7-5 7-6 4-6 8-6 |
| 1999-06-21 | Wimbledon | QF | grass | Pete Sampras | 4-6 2-1 |
| 1998-11-02 | Paris Masters | QF | hard | Pete Sampras | 6-3 6-3 |
| 1998-06-22 | Wimbledon | QF | grass | Pete Sampras | 7-6 6-4 6-4 |
| 1997-09-19 | Davis Cup WG SF: USA vs AUS | RR | hard | Pete Sampras | 6-1 6-2 7-6 |
| 1997-05-19 | Dusseldorf | RR | clay | Mark Philippoussis | 4-6 6-4 0-1 |
| 1996-08-26 | US Open | R16 | hard | Pete Sampras | 6-3 6-3 6-4 |
| 1996-01-15 | Australian Open | R32 | hard | Mark Philippoussis | 6-4 7-6(9) 7-6(3) |
| 1995-08-28 | US Open | R32 | hard | Pete Sampras | 6-7(5) 7-5 7-5 6-3 |
Averages over each player's completed matches in the selected window (200 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