Jan Michael Gambill defeated Justin Gimelstob 7-6 6-4 in the Singapore round of 32 on hard. The upset overturned the form book — Justin Gimelstob came in leading the head-to-head 4–3, defending last year's round of 16, but Jan Michael Gambill had been the form player, winning 2 of their last 5 on hard. Jan Michael Gambill narrowed the head-to-head to 4–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-01-03 | Chennai | R32 | hard | Justin Gimelstob | 6-3 6-3 |
| 2003-03-03 | Delray Beach | R16 | hard | Jan Michael Gambill | 7-5 7-5 |
| 2001-06-11 | Queen's Club | R32 | grass | Jan Michael Gambill | 6-3 7-5 |
| 2000-02-07 | San Jose | R32 | hard | Justin Gimelstob | 7-6(2) 6-2 |
| 1999-04-26 | Atlanta | R32 | hard | Justin Gimelstob | 6-0 6-4 |
| 1999-03-01 | Scottsdale | QF | hard | Jan Michael Gambill | 4-6 6-4 6-1 |
| 1999-02-08 | San Jose | R32 | hard | Justin Gimelstob | 6-3 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 194). ATP, WTA & Challenger.