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The prolific Dutchman enjoyed a remarkable playing career at United and lifted a Premier League title, an FA Cup and a League Cup under Sir Alex Ferguson.
Van Nistelrooy, who is widely regarded as one of the Premier League’s best strikers of all time, scored an incredible 150 times in 219 appearances for the Red Devils.
However, not even the 45-year-old former striker’s unbelievable finishing could help him when he came up against Milan in the Champions League.
Ferguson’s men visited the San Siro and the legendary former United manager had a squad stacked with incredible talent, including Cristiano Ronaldo, Ryan Giggs and Wayne Rooney.
Van Nistelrooy recalled how difficult it was to play against a merciless Italian team’s defence like Milan, with the Serie A club’s backline featuring Cafu, Jaap Stam, Nesta and Maldini.
Milan strengthened their back four with Gennaro Gattuso ahead of them, with Van Nistelrooy admitting that he thought they would ‘kill’ him if tried going for the ball.
“Italian defences were horrible to play against,” he told the Oxford Union in 2016.
“They all stay behind, it’s like, ‘Wow, go on full-backs, go forward a bit.’ And they are having none of it. They’d rather not concede than score!
“The defence I played against [of] Cafu, Jaap Stam, Alessandro Nesta and Paolo Maldini. That was incredible. And then they had [Gennaro] Gattuso in front of them. I thought they'd kill me if I got the ball.
“Oh, and then they had [Andrea] Pirlo and [Clarence] Seedorf, the strongest man in football. That was a tough night. I didn't get near a shot.”
Milan dumped United out of the Champions League after back-to-back wins in the round-of-16 matches.
Van Nistelrooy spent five seasons at Old Trafford and would leave United in 2006 after a heated fallout with Ferguson.
However, the United hero has since apologised to Ferguson and made amends with the 79-year-old iconic Scotsman.
Van Nistelrooy signed for Madrid in a reported £10.2m deal, but he was ravaged with injuries in the final 18 months of his time with Los Blancos.
Despite his injuries, Van Nistelrooy managed to score an impressive 64 times in 96 appearances and lifted two La Liga titles with the Spanish club.
The former United and Madrid striker spent two brief spells at Hamburger and Malaga before he announced his retirement from football in 2012.
Featured Image Credit: Oxford Union/PA
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