Justin Gimelstob defeated Jason Stoltenberg 3-6 6-3 6-4 in the Orlando round of 32 on clay. The upset overturned the form book — Jason Stoltenberg came in defending last year's semi-final. Justin Gimelstob extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | Cincinnati Masters | R64 | hard | Justin Gimelstob | 6-2 6-3 |
| 1999-04-19 | Orlando | R32 | clay | Jason Stoltenberg | 6-0 6-7(5) 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 (200 vs 138). ATP, WTA & Challenger.