6) AC Milan 4-1 Ajax: 1969, Santiago Bernabeu
In 1969, Ajax became the first ever Dutch club to be in a European Cup final but couldn't win the trophy that year.
Having the likes of Johan Cruyff at their disposal, Ajax were still the underdogs and rightly so. Facing AC Milan at that time was no joke. They were the team to be feared of as they had knocked out the previous two cup holders on their way to finals - Celtic in the quarter-finals and Manchester United in the semi-finals.
Ajax were completely blown away by Milan as the Italian side was 2 goals up in the first half. What else would you expect when you have the likes of Gianni Rivera and Pierino Prati in your attack.
Prati then went on to score a hattrick, the only player to so in the final till date and Milan comfortably won their 2nd European Cup.
Ajax did go on and win 3 consecutive European Cup from 1971 to 1973 but that night belonged to the Italian club.
AC Milan were just too hot for Ajax