In the 1956–57 season Symon took Rangers into the European Cup for the first time but it ended abruptly, going out on to French team OGC Nice. The following season saw Rangers suffer their worst ever defeat by their arch rivals Celtic, losing 7–1 in the League Cup final of 1957. They did however reach the semi-finals of the European Cup in 1960 losing eventually to German club Eintracht Frankfurt by a record aggregate 12–4 for a Scottish team. In 1961 Rangers became the first British team to reach a European final when they contested the Cup Winners' Cup final against Italian side Fiorentina, only to lose 4–1 on aggregate. Rangers suffered yet more despair in the final of the same competition in 1967, losing 1–0 after extra time to FC Bayern Munich.