Simon Roberts defeated Jamie Murray 7-6 7-5 in the Great Britain F12 round of 32 on hard. The upset overturned the form book — Jamie Murray came in leading the head-to-head 1–0. Simon Roberts claimed a first win over Jamie Murray in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-03 | Great Britain F14 | R32 | hard | Jamie Murray | 7-6(1) 6-2 |