Milan Pokrajac defeated Todd Paul 6-4 6-2 in the Canada F2 qualifying round on hard. The upset overturned the form book — Todd Paul came in leading the head-to-head 1–0. Milan Pokrajac claimed a first win over Todd Paul in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-04-07 | USA F7 | R32 | hard | Todd Paul | 6-1 6-4 |