Matthew Smith defeated Andrew Kennaugh 6-3 6-2 in the Great Britain 4 4 round of 32 on hard. The upset overturned the form book — Andrew Kennaugh came in leading the head-to-head 1–0, but Matthew Smith had been the form player, winning 4 of their last 8 on hard. Matthew Smith claimed a first win over Andrew Kennaugh in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-04-25 | Great Britain 2 1 | R16 | clay | Andrew Kennaugh | 6-7(3) 7-6(8) 6-1 |