Jonathan Marray defeated Matthew Smith 6-1 7-6 in the Great Britain F2 round of 32 on carpet. The upset overturned the form book — Matthew Smith came in leading the head-to-head 3–0. Jonathan Marray claimed a first win over Matthew Smith in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-04-03 | Great Britain F6 | R16 | hard | Matthew Smith | 1-6 6-3 6-4 |
| 2005-01-31 | Great Britain 1 Satellite 3 | R16 | hard | Matthew Smith | 7-6(4) 4-6 6-3 |
| 2001-09-17 | Great Britain F8 | R16 | hard | Matthew Smith | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.