Few players crossed Sir Alex Ferguson at Old Trafford and saw their Manchester United careers last much longer - just ask the likes of David Beckham and Jaap Stam.

Ruud van Nistelrooy is another player that falls into that category, despite the fact that he scored 150 goals during his five years with United.

The relationship between footballer and manager started to deteriorate at an alarming rate when Van Nistelrooy was benched for the 2006 League Cup final against Wigan Athletic, with Ferguson having preferred Louis Saha to partner Wayne Rooney in attack.

The Dutch centre-forward went on to be a substitute on a regular basis between that point and the end of the campaign, including the final encounter of the season against Charlton Athletic. Upon learning that he would not start the home fixture, Van Nistelrooy stormed away from the ground and was not involved at all.

It would prove to be his last act as a United player as clubs started to circulate for his services. The rumour was that Bayern Munich were keen, but Van Nistelrooy had set his heart on Real Madrid. The Spaniards saw their first bid rejected, but a second offer of £11m was accepted by their English counterparts and so eight years ago today, the 30-year-old signed on at the Bernabeu.

"It's a great honour to stand here in the Bernabeu. It's a dream come true," Van Nistelrooy told reporters at his unveiling press conference. Then, asked whether he wanted to leave United because he felt that he didn't have the support of Ferguson that other United players had been given, he replied: "You summed up my feelings quite well. When we played the final, that's when I started to feel unhappy."

Madrid president Ramon Calderon added: "We have a perfect striker who combines efficiency and power with great footballing technique."

His first two seasons in La Liga were successful, with the striker scoring 53 goals in all competitions. Thereafter, injuries started to take hold and and in January 2010 he was sold to Hamburg, before he retired in May 2012 following a season with Malaga.

In terms of his understanding with Ferguson, Van Nistelrooy has since patched up his differences with the Scot.