Daskalakis began his career at his local side OFI, playing mostly as a back-up goalkeeper to Michalis Sifakis.
[1] His steady performances with Ergotelis drew the attention of Greek champions Olympiacos, who signed Daskalakis in the summer of 2011 to be the back-up of Franco Costanzo.
Daskalakis made only a single appearance for the club during the season, as he ended up being back-up to third-choice keeper Balázs Megyeri, after Costanzo's contract was terminated.
In 2012, Daskalakis signed a contract with freshly promoted Superleague side Veria,[2] but was immediately sidelined after conceding two goals in his debut vs. his former club Olympiacos.
[4] His second spell at OFI however, was also abruptly terminated after a dispute with manager Gennaro Gattuso, who allegedly requested Daskalakis and teammate Michail Fragoulakis to be expelled from the club.