Born in Piraeus, Greece, Andrianopoulos began his career at the age of 18, playing for local club Peiraikos Syndesmos.

Peiraikos Syndesmos merged with Peiraiki Enosis in January 1924 and the Athletic and Football Club of Piraeus was formed.

The same year around autumn, the new club split in two different squads: One team, led by the Andrianopoulos brothers and goalkeeper Kostas Klidouchakis, formed Olympiacos Omilos, which evolved into Olympiacos;[2] the other, led by Kostas Ferlemis, Christos Peppas and Giorgos Chatziandreou merged, with an independent club named "Young Boys" to form Peiraikos Omilos, which in turn evolved into Ethnikos Piraeus.

Giannis, Georgios, Konstantinos and Vasilios, Leonidas went on to make the newly formed Piraeus Club famous throughout Greece.

As a result, Yiannis and his brothers earned Olympiacos the name Thrylos meaning "Legend" in Greek, a nickname which the club carries to this day.