Todd Paul defeated Milan Pokrajac 6-1 6-4 in the USA F7 round of 32 on hard. The upset overturned the form book — Milan Pokrajac came in leading the head-to-head 1–0. Todd Paul claimed a first win over Milan Pokrajac in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-03-10 | Canada F2 | QF | hard | Milan Pokrajac | 6-4 6-2 |