Petros Tsitsipas defeated Michal Dembek 5-7 6-2 7-6 in the M15 Heraklion 1 round of 32 on hard. The upset overturned the form book — Michal Dembek came in leading the head-to-head 1–0. Petros Tsitsipas claimed a first win over Michal Dembek in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-09 | M15 Heraklion 1 | R16 | hard | Michal Dembek | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.