Matthew Illingworth defeated Colin Fleming 6-4 7-5 in the Great Britain F17 round of 16 on hard. The upset overturned the form book — Colin Fleming came in leading the head-to-head 1–0. Matthew Illingworth claimed a first win over Colin Fleming in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-08 | Great Britain F14 | R16 | hard | Colin Fleming | 6-7(5) 7-5 7-6(2) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.