Daskalakis was born on November 18, 1977 in Athens. He started his career at Asteras Zografou and later moved to Ilisiakos but his greatest games were played in Cyprus between 2000 and 2008 for APOEL. After leaving the yellow-blues of Lefkosia, Daskalakis played for one year with AEK Larnaca. In January of 2009, he returned to mainland Greece to play for Ethnikos Asteras in the Greek Football B Division. Later in the year he signed for Olympiakos Nicosia.
Though a central defender, he can score an occasional goal.
Daskalakis has so far (August 2011) been capped 11 times by the Cypriot National Football Team.