Oliver Golding defeated Joshua Milton 6-3 6-2 in the Wimbledon q128 on grass. The upset overturned the form book — Joshua Milton came in leading the head-to-head 3–0. Oliver Golding claimed a first win over Joshua Milton in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-06-30 | Great Britain F12 | QF | grass | Joshua Milton | 1-6 6-4 7-5 |
| 2011-10-17 | Great Britain F16 | R16 | hard | Joshua Milton | 6-4 6-4 |
| 2009-06-13 | Eastbourne | Q16 | grass | Joshua Milton | 6-2 6-2 |
Averages over each player's completed matches in the selected window (6 vs 40). 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