Jamie Murray defeated Simon Roberts 7-6 6-2 in the Great Britain F14 round of 32 on hard. The upset overturned the form book — Simon Roberts came in leading the head-to-head 1–0, but Jamie Murray had been the form player, winning 3 of their last 8 on hard. Jamie Murray claimed a first win over Simon Roberts in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-09-19 | Great Britain F12 | R32 | hard | Simon Roberts | 7-6(5) 7-5 |