Mark Philippoussis defeated Justin Gimelstob 7-6 6-4 in the San Jose quarter-final on hard. The result followed the form book — Mark Philippoussis came in leading the head-to-head 2–1, defending the title. Mark Philippoussis extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-10 | Newport | F | grass | Mark Philippoussis | 6-3 7-5 |
| 2000-07-24 | Los Angeles | R16 | hard | Justin Gimelstob | 3-6 7-6(5) 7-6(3) |
| 1999-02-08 | San Jose | QF | hard | Mark Philippoussis | 6-2 3-6 7-6(0) |
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 151). ATP, WTA & Challenger.