Alex Obrien defeated Gustavo Kuerten 6-3 7-6 in the Canada Masters round of 64 on hard. The upset overturned the form book — Gustavo Kuerten came in leading the head-to-head 1–0, defending last year's final, but Alex Obrien had been the form player, winning 2 of their last 8 on hard. Alex Obrien claimed a first win over Gustavo Kuerten in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-08-17 | New Haven | R32 | hard | Gustavo Kuerten | 6-3 6-2 |
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 (42 vs 200). ATP, WTA & Challenger.