Andrew Kennaugh defeated Matthew Smith 6-7 7-6 6-1 in the Great Britain 2 1 round of 16 on clay. The upset overturned the form book — Matthew Smith came in leading the head-to-head 1–0. Andrew Kennaugh claimed a first win over Matthew Smith in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-24 | Great Britain 4 4 | R32 | hard | Matthew Smith | 6-3 6-2 |