Jan Siemerink defeated Justin Gimelstob 4-6 6-2 7-5 in the Orlando round of 32 on clay. The upset overturned the form book — Justin Gimelstob came in leading the head-to-head 2–0, defending last year's round of 32. Jan Siemerink claimed a first win over Justin Gimelstob in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-09-11 | Tashkent | R32 | hard | Justin Gimelstob | 6-4 6-3 |
| 1997-09-22 | Toulouse | R16 | hard | Justin Gimelstob | 3-6 7-6(7) 6-0 |
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 (51 vs 151). ATP, WTA & Challenger.