It is the most successful Greek team . It has won thirty-seven League titles , twenty-four Greek Cups and three Greek Super Cups , more titles than any other Greek team and it is one of four teams that have never been relegated from the first division . Olympiacos is the most successful club in Greek football history , having won 38 League titles , 24 Greek Cups and 4 Greek Super Cups , more titles than any other Greek team and it is one of four teams that have never been relegated from the first division ; in European competitions , they have reached the quarter-finals twice , in the 1998 â `` 99 UEFA Champions League and the 1992 â `` 93 European Cup Winners ' Cup .