Chris Eaton defeated Ian Flanagan 6-4 2-6 6-2 in the Great Britain 1 1 round of 16 on hard. The upset overturned the form book — Ian Flanagan came in leading the head-to-head 2–0. Chris Eaton claimed a first win over Ian Flanagan in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-11-05 | Great Britain F21 | R32 | hard | Ian Flanagan | 6-4 7-5 |
| 2007-08-06 | Great Britain F14 | R32 | hard | Ian Flanagan | 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.