Jan Michael Gambill defeated Mark Philippoussis 6-4 6-4 6-4 in the US Open round of 64 on hard. The result followed the form book — Jan Michael Gambill came in leading the head-to-head 3–1, defending last year's round of 64. Jan Michael Gambill extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-20 | Miami Masters | R16 | hard | Jan Michael Gambill | 6-2 6-7(6) 6-3 |
| 1999-11-08 | Stockholm | QF | hard | Jan Michael Gambill | 4-6 6-2 7-5 |
| 1999-06-07 | Queen's Club | R32 | grass | Mark Philippoussis | 2-6 6-3 6-4 |
| 1998-03-09 | Indian Wells Masters | R64 | hard | Jan Michael Gambill | 7-6(7) 5-7 7-6(6) |
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.