Kyle Brassington defeated Joshua Milton 6-3 3-6 6-3 in the Great Britain F13 round of 32 on grass. The upset overturned the form book — Joshua Milton came in leading the head-to-head 2–0, but Kyle Brassington had been the form player, winning 3 of their last 6 on grass. Kyle Brassington claimed a first win over Joshua Milton in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-07-13 | Great Britain F9 | SF | grass | Joshua Milton | 6-2 6-2 |
| 2008-07-07 | Great Britain F9 | R32 | grass | Joshua Milton | 7-5 3-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.