Gustavo Kuerten defeated Justin Gimelstob 7-6 4-6 6-1 in the San Jose round of 32 on hard. The upset overturned the form book — Justin Gimelstob came in defending last year's round of 16. Gustavo Kuerten extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-13 | Indian Wells Masters | R64 | hard | Gustavo Kuerten | 7-5 3-6 6-3 |
| 1997-06-23 | Wimbledon | R128 | grass | Justin Gimelstob | 6-3 6-4 4-6 1-6 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 200). ATP, WTA & Challenger.