Mark Philippoussis defeated Andre Agassi 6-3 2-6 6-7 6-3 6-4 in the Wimbledon round of 16 on grass. The upset overturned the form book — Andre Agassi came in leading the head-to-head 6–1, defending last year's round of 64. Mark Philippoussis narrowed the head-to-head to 6–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-03-17 | Miami Masters | R16 | hard | Andre Agassi | 4-6 6-3 6-2 |
| 2003-02-10 | San Jose | R16 | hard | Andre Agassi | 6-4 6-1 |
| 2000-06-26 | Wimbledon | QF | grass | Andre Agassi | 7-6(4) 6-3 6-4 |
| 2000-01-17 | Australian Open | R16 | hard | Andre Agassi | 6-4 7-6(4) 5-7 6-3 |
| 1999-11-01 | Paris Masters | QF | hard | Andre Agassi | 6-4 6-1 |
| 1999-10-25 | Stuttgart Masters | R32 | carpet | Andre Agassi | 6-2 6-4 |
| 1997-03-10 | Indian Wells Masters | R64 | hard | Mark Philippoussis | 7-6(5) 7-6(5) |
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 (113 vs 173). ATP, WTA & Challenger.