Mark Philippoussis defeated Tim Henman 6-1 5-7 6-7 6-3 6-4 in the Wimbledon round of 16 on grass. The result followed the form book — Mark Philippoussis came in leading the head-to-head 3–2, defending last year's quarter-final. Mark Philippoussis extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-06-21 | Wimbledon | R16 | grass | Tim Henman | 6-2 7-5 6-7(3) 7-6(5) |
| 2001-12-31 | Adelaide | F | hard | Tim Henman | 6-4 6-7(6) 6-3 |
| 1999-11-01 | Paris Masters | R16 | hard | Mark Philippoussis | 6-1 3-6 6-3 |
| 1998-08-31 | US Open | R16 | hard | Mark Philippoussis | 7-5 0-6 6-4 6-1 |
| 1997-09-29 | Basel | SF | hard | Mark Philippoussis | 7-6(2) 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.