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Featured Image Credit: PA
The 44-year-old Manchester United legend was widely revered for his deadly finishing and is one of the best strikers in the history of the Premier League.
But even Van Nistelrooy had his work cut out for him when he came up against Milan in the Champions League.
United travelled to the San Siro with a squad that boasted talents like Cristiano Ronaldo, Ryan Giggs, Wayne Rooney and Van Nistelrooy.
Van Nistelrooy admitted that he thought the Milan backline, strengthened by Gennaro Gattuso ahead of them, would 'kill him' if he touched the ball.
The former Netherlands international told the Oxford Union: "Italian defences were horrible to play against.
"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 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."
United lost both round-of-16 matches to Milan and crashed out of the competition 2-0 on aggregate.
Van Nistelrooy spent five years at Old Trafford and won a Premier League title, a League Cup and an FA Cup.
The Dutchman, who had a high-profile fallout with Sir Alex Ferguson, left United and spent four years with Real Madrid.