Jan Michael Gambill defeated Stefan Koubek 6-4 3-6 6-2 in the Long Island round of 32 on hard. The result followed the form book — Jan Michael Gambill came in leading the head-to-head 3–2, defending last year's round of 32. Jan Michael Gambill extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-08-16 | Washington | R32 | hard | Jan Michael Gambill | 7-5 6-4 |
| 2003-03-17 | Miami Masters | R128 | hard | Jan Michael Gambill | 2-6 6-3 6-2 |
| 2002-12-30 | Doha | F | hard | Stefan Koubek | 6-4 6-4 |
| 2000-02-28 | Delray Beach | R16 | hard | Stefan Koubek | 6-1 7-6(7) |
| 1999-08-30 | US Open | R128 | hard | Jan Michael Gambill | 7-5 6-1 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 (157 vs 200). ATP, WTA & Challenger.