Colin Fleming defeated Colin Obrien 3-6 7-5 6-4 in the Greece F5 round of 32 on carpet. The result followed the form book — Colin Fleming came in leading the head-to-head 2–0. Colin Fleming extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-31 | Great Britain F12 | QF | hard | Colin Fleming | 7-5 6-1 |
| 2008-09-08 | Great Britain F14 | QF | hard | Colin Fleming | 6-2 1-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.