Lester Cook defeated Philip Gubenco 6-4 7-5 in the Canada F1 round of 32 on hard. The upset overturned the form book — Philip Gubenco came in leading the head-to-head 1–0. Lester Cook claimed a first win over Philip Gubenco in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-03 | USA F25 | R32 | hard | Philip Gubenco | 6-3 2-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.