Dimitar Kutrovsky defeated Oscar Fabian Matthews 6-7 7-5 7-5 in the USA F12 round of 32 on hard. Dimitar Kutrovsky extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-11-17 | Mexico F13 | R16 | hard | Oscar Fabian Matthews | 6-4 5-7 7-6(6) |
| 2014-04-07 | USA F11 | R16 | hard | Dimitar Kutrovsky | 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.