Matthew Roberts defeated Christoph Palmanshofer 6-4 6-3 in the Costa Rica F1 round of 32 on hard. The upset overturned the form book — Christoph Palmanshofer came in leading the head-to-head 1–0. Matthew Roberts claimed a first win over Christoph Palmanshofer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-01-28 | Mexico F2 | R16 | hard | Christoph Palmanshofer | 6-4 6-2 |