Simon Larose defeated Huntley Montgomery 4-6 7-6 6-3 in the USA F2 round of 32 on hard. The upset overturned the form book — Huntley Montgomery came in leading the head-to-head 1–0. Simon Larose 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 | SF | hard | Huntley Montgomery | 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.