Philip Gubenco defeated Lester Cook 6-3 2-6 6-3 in the USA F25 round of 32 on hard. The upset overturned the form book — Lester Cook came in leading the head-to-head 1–0. Philip Gubenco claimed a first win over Lester Cook in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-03-06 | Canada F1 | R32 | hard | Lester Cook | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.