Mark Philippoussis defeated Jan Michael Gambill 2-6 6-3 6-4 in the Queen's Club round of 32 on grass. The upset overturned the form book — Jan Michael Gambill came in leading the head-to-head 4–0, defending last year's round of 32. Mark Philippoussis claimed a first win over Jan Michael Gambill in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-28 | US Open | R64 | hard | Jan Michael Gambill | 6-4 6-4 6-4 |
| 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 |
| 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.