Alongside Predrag Đorđević, Anatolakis is one of two Olympiacos players to have been part of all nine of their Greek championship victories since 1996.
Produced by Ethnikos Pylaias, Anatolakis first appeared in the Greek top flight as an 18-year-old for Iraklis FC in the 1992/93 season, going on to make a further 133 outings for the Thessalonika-based team prior to a move to Olympiacos during 1996/97.
A fearsome competitor, he was a key squad member as Olympiacos won every title from then until 2003/04, and the following season Anatolakis had his finest hour as the league championship was regained.
His contribution to their double-winning campaign was rewarded with a two-year contract extension, and the following season the league and Greek Cup were captured again.
Many thought that would be the start of a lengthy career but he was subsequently more out of the side than in and did not appear from 1999 until October 2005, when he was a substitute in a 1-0 FIFA World Cup qualifying win against Georgia.