Ross Hutchins defeated Ian Flanagan 6-2 7-6 in the Great Britain F5 round of 32 on hard. Ross Hutchins extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-09-19 | Great Britain F12 | R32 | hard | Ross Hutchins | 7-6(6) 6-2 |
| 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.