Todd Paul defeated Brett Joelson 7-5 7-6 in the Canada F1 round of 16 on hard. The upset overturned the form book — Brett Joelson came in leading the head-to-head 1–0. Todd Paul claimed a first win over Brett Joelson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-11-03 | USA F28 | R32 | hard | Brett Joelson | 5-7 6-3 7-6(4) |