Both sides had a connection to the early history of European football ; Chelsea were invited to take part in the inaugural European Cup in 1955 – 56 as champions of England , only to be denied entry by The Football League , allowing Manchester United to become the first English entrants in the competition the following season . In February 1958 , eight Manchester United players were killed in the Munich air disaster , when the aeroplane carrying their team back from a match in Belgrade crashed while attempting to take off from a refuelling stop in Munich . Manager Matt Busby was seriously injured in the crash and almost died as a result , but he rebuilt the team , and in May 1968 , Manchester United became the first English winners of the European Cup , beating Benfica 4 – 1 in the 1968 European Cup Final . Chelsea won their first European trophy three years later , when they beat Real Madrid 2 – 1 in the 1971 European Cup Winners ' Cup Final replay after a 1 – 1 draw in the first match . Both Chelsea and Manchester United won that same competition during the 1990s – first Manchester United beat Barcelona 2 – 1 in the 1991 final ( followed by victory over Red Star Belgrade in the 1991 Super Cup ) , and then Chelsea beat VfB Stuttgart in the 1998 final ( followed by victory over Real Madrid in the 1998 Super Cup , their most recent European success at the time ) . Manchester United then won their second European Cup the following year , beating Bayern Munich in the 1999 Champions League final
Munich air disaster
Munich air disaster
2008 UEFA Champions League Final