Manchester United, Bayern Munich, AC Milan and PSV Eindhoven booked their places in the Champions League quarter-finals on Wednesday, dashing English hopes of making European football history.
United beat Lille 1-0 at Old Trafford for a 2-0 aggregate win, ending an acrimonious knockout round tie, and Bayern stormed back from a 3-2 defeat in Spain to beat Real 2-1 on the night and qualify on the away goals rule after a 4-4 aggregate.
It was a classic encounter between two European heavyweights and the tone was set when Roy Makaay put Bayern ahead after 10 seconds - the fastest goal in Champions League history.
Manchester United reached the quarter-finals for the first time in four years. Henrik Larsson, playing his last competitive match for United at Old Trafford before the end of his loan spell from Helsingborg, was left unmarked after 72 minutes and made no mistake with a well-taken header from a pinpoint Cristiano Ronaldo cross.
PSV drew 1-1 at Arsenal, their defender Alex scoring an own goal and then the vital late equaliser to secure a 2-1 win over the two legs and deny England the chance of becoming the first country to put four clubs into the last eight.
Both last year's finalists are out, as runners-up Arsenal join Barcelona, knocked out by Liverpool, on the sidelines.
AC Milan and Celtic finished a thrilling 90 minutes with the score 0-0, and the same on aggregate, forcing their game into extra time at San Siro.
Milan won it in extra time as their Brazilian playmaker Kaka scored a fine winner in the 93rd minute after the teams had been goalless for 180 minutes.
United, Bayern and PSV will join 2005 winners Liverpool, Chelsea, AS Roma and Valencia, who all qualified on Tuesday, in the quarter-final and semi-final draw.
That draw will be held on Friday in Athens, which is also hosting the final on May 23.