Joshua Milton defeated Richard Bloomfield 4-6 7-6 6-3 in the Great Britain F15 round of 32 on hard. The upset overturned the form book — Richard Bloomfield came in leading the head-to-head 1–0. Joshua Milton claimed a first win over Richard Bloomfield in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-11-03 | Great Britain F18 | SF | hard | Richard Bloomfield | 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.