Richard Irwin advanced when Colin Fleming retired 4-0 in the Great Britain F11 qualifying round. Richard Irwin claimed a first win over Colin Fleming in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-10 | Great Britain F9 | R16 | grass | Colin Fleming | 6-3 6-4 |
| 2006-01-30 | Great Britain 1 2 | R32 | hard | Colin Fleming | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.