Joshua Milton advanced past Richard Bloomfield via walkover in the Great Britain F13 qualifying round. Joshua Milton extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-07-29 | Great Britain F15 | R32 | hard | Joshua Milton | 4-6 7-6(4) 6-3 |
| 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.