Dimitar Kutrovsky defeated Oscar Fabian Matthews 6-1 6-2 in the USA F11 round of 16 on hard. Dimitar Kutrovsky extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-04-06 | USA F12 | R32 | hard | Dimitar Kutrovsky | 6-7(4) 7-5 7-5 |
| 2014-11-17 | Mexico F13 | R16 | hard | Oscar Fabian Matthews | 6-4 5-7 7-6(6) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.