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.
In 2010 he joined PAEEK for one year and then joined Ethnikos Assias for one year. In the summer of 2012 he returned once again to Greece, now to play for Ergotelis on the island of Crete. His contract ended in January 2013 leaving him without a club for six months. In the summer of 2014 he signed his last contract at Ethnikos Latsion, where he ended his career in 2015.
Though a central defender, he could score an occasional goal.
Daskalakis has been capped 12 times by the Cypriot National Football Team.