Joshua Milton defeated Pablo Figueroa 6-3 6-3 in the Sweden F4 qualifying round on hard. Joshua Milton extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-09-22 | Sweden F5 | R32 | hard | Pablo Figueroa | 6-3 7-6(2) |
| 2012-09-24 | Sweden F6 | SF | hard | Joshua Milton | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.