Ross Hutchins defeated Ian Flanagan 7-6 6-2 in the Great Britain F12 round of 32 on hard. Ross Hutchins extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-03-27 | Great Britain F5 | R32 | hard | Ross Hutchins | 6-2 7-6(7) |
| 2004-09-27 | Great Britain F5 | R16 | hard | Ian Flanagan | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.