The eldest of the Andrianopoulos brothers was born in 1900. He started his career in 1918 with Peiraikos Syndesmos, winning an unofficial Greek title in 1923. The following year, Peiraikos Syndesmos merged with Peiraiki Enosis to form the Athletic and Football Club of Piraeus. Andrianopoulos won the Athens-Piraeus title with his new club which dissolved that same year (Autumn 1924). Andrianopoulos and his brothers then founded Olympiakos Omilos and, in March 1925, Olympiakos FC. Besides a footballer, Yiannis was also Olympiakos' coach from 1925 - 1927. Upon his retirement from football in 1929, he became President of Olympiakos (1932 - 1935).