#3 Middlesbrough vs Manchester United – 2002
Manchester United have 18 wins, two draws and two defeats on Boxing Day in the Premier League era. One of those defeats was inspired by one of their own. Steve Mclaren, who was Sir Alex Ferguson’s assistant at Old Trafford, was the manager of Middlesbrough and oversaw a Boxing Day humbling of his former employers.
Alen Boksic and Szilard Nemeth had given Boro a 2-0 lead early in the second half, but United, as was the norm, mounted a fightback. Ryan Giggs pulled one back and the Red Devils looked to be well and truly back in the game.
But Joseph-Desire Job gave Boro a 3-1 lead to top off a season in which they had already beaten Liverpool, Tottenham and Manchester City.
That loss put United seven points behind Arsenal. But in the second half of the season, they rallied brilliantly to eventually win the title by five points.