Philip Gubenco defeated Huntley Montgomery 6-2 1-6 7-6 in the Canada F3 semi-final on hard. The upset overturned the form book — Huntley Montgomery came in leading the head-to-head 1–0. Philip Gubenco claimed a first win over Huntley Montgomery in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-16 | Canada F2 | R32 | hard | Huntley Montgomery | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.