Henry Craig defeated Michail Pervolarakis 5-7 7-6 6-3 in the M15 Heraklion 3 round of 16 on hard. The upset overturned the form book — Michail Pervolarakis came in leading the head-to-head 2–0, but Henry Craig had been the form player, winning 5 of their last 9 on hard. Henry Craig claimed a first win over Michail Pervolarakis in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-31 | M15 Heraklion 4 | QF | hard | Michail Pervolarakis | 6-4 6-7(5) 6-4 |
| 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.