Chris Woodruff defeated Mark Philippoussis 6-4 6-4 in the Vienna round of 32 on hard. The upset overturned the form book — Mark Philippoussis came in leading the head-to-head 5–1. Chris Woodruff narrowed the head-to-head to 5–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Hong Kong | R16 | hard | Mark Philippoussis | 6-7(4) 7-5 6-3 |
| 2000-03-13 | Indian Wells Masters | R64 | hard | Mark Philippoussis | 6-3 6-4 |
| 1999-03-08 | Indian Wells Masters | SF | hard | Mark Philippoussis | 6-1 6-2 |
| 1999-02-15 | Memphis | R32 | hard | Mark Philippoussis | 6-3 7-6(3) |
| 1997-07-28 | Canada Masters | QF | hard | Chris Woodruff | 6-4 6-4 |
| 1997-03-03 | Scottsdale | SF | hard | Mark Philippoussis | 4-6 7-6(5) 6-2 |
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 (163 vs 200). ATP, WTA & Challenger.