Huntley Montgomery defeated Philip Gubenco 7-5 6-2 in the Canada F2 round of 32 on hard. The upset overturned the form book — Philip Gubenco came in leading the head-to-head 1–0, but Huntley Montgomery had been the form player, winning 3 of their last 4 on hard. Huntley Montgomery claimed a first win over Philip Gubenco in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-23 | Canada F3 | SF | hard | Philip Gubenco | 6-2 1-6 7-6(2) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.