Andrew Roberts defeated Nima Roshan 6-4 7-6 in the USA F19 round of 32 on hard. The upset overturned the form book — Nima Roshan came in leading the head-to-head 1–0. Andrew Roberts claimed a first win over Nima Roshan in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-19 | Mexico F8 | R16 | hard | Nima Roshan | 6-4 7-6(5) |