Colin Fleming defeated Colin Obrien 7-5 6-1 in the Great Britain F12 qualifying round on hard. 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 |
|---|---|---|---|---|---|
| 2008-09-22 | Greece F5 | R32 | carpet | Colin Fleming | 3-6 7-5 6-4 |
| 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.