Gallery: Bernabeu battles
Manchester United and Real Madrid are two of the biggest names in world football, yet meetings between the sides are relatively rare.
Indeed, Wednesday’s last 16, first-leg clash will be only the fifth time the Reds have played at the Bernabeu since first visiting in April 1957.
That night Sir Matt Busby’s men suffered a 3-1 first-leg defeat in the semi-finals of the club’s first ever European Cup foray, eventually bowing out 5-3 on aggregate.
Sir Matt had to wait more than a decade for another crack at Los Blancos and this time, after a 1-0 first-leg win at Old Trafford, his side claimed a famous 3-3 draw to reach the final for the first time.
Sir Alex Ferguson has taken his men to the Bernabeu twice before, though he’s yet to taste victory there. In the 2000 quarter-finals, the Reds claimed a creditable goalless draw but were outclassed in the second leg at Old Trafford.
Three years later, again in the last eight, United went down 3-1 in Spain and, despite a rousing second-leg display, lost 6-5 on aggregate.
United’s previous games at the Bernabeu:
11/04/57: Real 3-1 United
15/05/68: Real 3-3 United
04/04/00: Real 0-0 United
08/04/03: Real 3-1 United
Ray Wood saves under pressure from Alfredo Di Stefano in the first leg of the 1957 European Cup semi-final, which Real won 3-1.
Sir Matt Busby in the Bernabeu before the European Cup semi-final, second leg against Real in April 1968
Brian Kidd rises to head the ball in the 1968 clash.
David Sadler back-heels United’s second goal in a 3-3 draw.
United’s players wave to the crowd after the draw, which sent the Reds through to the final 4-3 on aggregate.
Gary Neville battles with Savio as Roy Keane looks on during the quarter-final first leg in April 2000, which finished goalless.
Paul Scholes takes the ball forward during the same game.
David Beckham thanks the travelling United fans for their support at the end of the game.
Fabien Barthez can only watch as Luis Figo puts Real ahead in April 2003.
Ruud van Nistelrooy scored United’s only goal in a 3-1 first-leg defeat.
Wes Brown and Rio Ferdinand look to thwart Ronaldo in the quarter-final encounter.
David Beckham gets above Roberto Carlos in the same game.
Ryan Giggs controls the ball at the Bernabeu but Real took the upper hand and won the tie 6-5 on aggregate.