Born in Chania, Dentakis came through the academy at Kissamikos and turned professional at Platanias, making his Super League debut with the club at the age of 19. After a few stops through local sides in Crete, Dentakis eventually landed at Volos, helping the club make two consecutive promotions from Gamma Ethniki to the Super League, and would remain a regular for them in the top flight. He would win another promotion to the Super League with Levadiakos in 2023/24. Over his career, Dentakis had made 77 total appearances in the Super League with Platanias, Volos, Apollon, Levadiakos, and most recently Lamia, before joining AKFC in July 2025.