Richard Fromberg defeated Justin Gimelstob 4-6 7-6 6-2 in the Delray Beach quarter-final on hard. The upset overturned the form book — Justin Gimelstob came in leading the head-to-head 1–0, defending last year's round of 16. Richard Fromberg claimed a first win over Justin Gimelstob in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Washington | R64 | hard | Justin Gimelstob | 6-4 2-6 7-6(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 (47 vs 151). ATP, WTA & Challenger.