Vincent Spadea defeated Mark Philippoussis 6-4 6-3 in the San Jose round of 32 on hard. The upset overturned the form book — Mark Philippoussis came in leading the head-to-head 4–1. Vincent Spadea narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-02 | Adelaide | R32 | hard | Mark Philippoussis | 6-4 3-6 6-4 |
| 2004-05-17 | Dusseldorf | RR | clay | Mark Philippoussis | 6-7(1) 6-3 7-6(4) |
| 2002-05-06 | Rome Masters | R64 | clay | Mark Philippoussis | 6-2 6-2 |
| 1999-05-10 | Rome Masters | R64 | clay | Vincent Spadea | 7-6(2) 4-6 6-1 |
| 1997-09-22 | Toulouse | SF | hard | Mark Philippoussis | 7-5 6-4 |
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.