Mark Philippoussis defeated Pete Sampras 4-6 7-5 7-6 4-6 8-6 in the Roland Garros round of 128 on clay. The upset overturned the form book — Pete Sampras came in leading the head-to-head 4–1, defending last year's round of 64. Mark Philippoussis narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 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 143). ATP, WTA & Challenger.