Joshua Milton defeated Daniel Smethurst 7-5 6-1 in the Great Britain F8 qualifying round on hard. The upset overturned the form book — Daniel Smethurst came in leading the head-to-head 4–3. Joshua Milton narrowed the head-to-head to 4–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-01-19 | Great Britain F1 | QF | hard | Daniel Smethurst | 6-4 7-6(1) |
| 2014-11-03 | Great Britain F19 | SF | hard | Joshua Milton | 1-6 6-4 6-3 |
| 2014-01-20 | Great Britain F2 | R32 | hard | Daniel Smethurst | 6-3 6-3 |
| 2012-10-15 | USA F28 | R32 | hard | Joshua Milton | 6-3 5-7 6-1 |
| 2012-09-24 | Sweden F6 | F | hard | Daniel Smethurst | 4-6 6-0 6-1 |
| 2011-10-24 | Great Britain F17 | R32 | hard | Joshua Milton | 6-4 6-3 |
| 2010-02-15 | Spain F6 | R32 | clay | Daniel Smethurst | 6-3 6-2 |
Averages over each player's completed matches in the selected window (43 vs 15). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About