Michail Pervolarakis defeated Henry Craig 6-4 6-7 6-4 in the M15 Heraklion 4 quarter-final on hard. Michail Pervolarakis extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-23 | M15 Heraklion 3 | R16 | hard | Henry Craig | 5-7 7-6(4) 6-3 |
| 2019-05-12 | M15 Heraklion 1 | F | hard | Michail Pervolarakis | 6-2 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.