Colin Fleming defeated Matthew Illingworth 6-7 7-5 7-6 in the Great Britain F14 round of 16 on hard. The upset overturned the form book — Matthew Illingworth came in leading the head-to-head 1–0, but Colin Fleming had been the form player, winning 2 of their last 5 on hard. Colin Fleming claimed a first win over Matthew Illingworth in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-27 | Great Britain F17 | R16 | hard | Matthew Illingworth | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.