Todd Paul defeated Kaden Hensel 6-3 1-6 7-5 in the Canada F1 qualifying round on hard. The upset overturned the form book — Kaden Hensel came in leading the head-to-head 1–0, but Todd Paul had been the form player, winning 4 of their last 8 on hard. Todd Paul claimed a first win over Kaden Hensel in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-03-16 | Canada F3 | R32 | hard | Kaden Hensel | 6-3 6-4 |