Tom Rushby defeated Simon Roberts 6-2 6-4 in the Great Britain 2 4 round of 32 on hard. The upset overturned the form book — Simon Roberts came in leading the head-to-head 2–0. Tom Rushby claimed a first win over Simon Roberts in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-10 | Great Britain F15 | R32 | hard | Simon Roberts | 7-6(4) 6-4 |
| 2005-01-31 | Great Britain 1 Satellite 2 | R32 | hard | Simon Roberts | 6-2 6-7(5) 6-3 |