Jan Michael Gambill defeated Gustavo Kuerten 7-6 6-4 in the Indian Wells Masters round of 16 on hard. The upset overturned the form book — Gustavo Kuerten came in leading the head-to-head 2–0, defending last year's round of 32, but Jan Michael Gambill had been the form player, winning 3 of their last 8 on hard. Jan Michael Gambill claimed a first win over Gustavo Kuerten in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Hamburg Masters | R32 | clay | Gustavo Kuerten | 6-4 6-4 |
| 1998-02-16 | Memphis | R16 | hard | Gustavo Kuerten | 6-4 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 (200 vs 200). ATP, WTA & Challenger.