Apostolakis was no stranger to controversy as a player, his switch from Olympiacos to Panathinaikos in 1990 led to the cancellation of the Greek Super Cup as the authorities feared riots.

As a footballer he played his best years for Panathinaikos being one of the key players behind club's European runs in 1991–92 and 1995–96.

During his playing career, Apostolakis was capped 96 times by the Greece national team scoring five goals.

His 96 caps stood as a Greek record until it was broken by Theodoros Zagorakis.

Apostolakis is the father of Kostas, who plays as a professional footballer at Panathinaikos.