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The term upset is simply defined as “an unexpected defeat,” but in sports it can mean so much more. For the favorite, it’s about the pressure that comes with heightened expectations. For the underdog, it’s about using those expectations as motivation. As part of our ongoing Decade Debate series, here is a list of the ten biggest upsets of the last ten years. Remember, the magnitude of the stage is just as important as the perceived disparity between the two parties involved, so extra points are given to upsets that occurred in the postseason or in a title game.

10. Federer beats Sampras at the 2001 Wimbledon

By 2001, the sports world had begun to question Pete Sampras’ ability as a dominant tennis player. The man was just 29 years old and the owner of 13 Grand Slam titles, but critics predicted an oncoming collapse. Since winning the Australian Open in 1997, Pistol Pete’s Grand Slam championships curiously only came at Wimbledon. In fact, Sampras had captured all but one Wimbledon championship since his first appearance in 1993. Naturally, if he was a sure bet anywhere, it was at the All England Club. While most will remember this time period as the declining stage of Sampras’ career, it also marked the beginning of Roger Federer’s success as a professional. After winning the Wimbledon juniors in 1998, Federer was often viewed as the likely heir to Sampras’ throne. Still, nobody expected the 19 year-old and the Grand Slam record holder to clash at Wimbledon in 2001. Furthermore, if they did happen to meet, Federer wasn’t supposed to win. Making his Centre Court debut, Federer defeated Sampras 7-6 (7), 5-7, 6-4, 6-7 (2), 7-5, thereby snapping Sampras’ 31-match winning streak at Wimbledon. Sure, it was only a fourth round match, but it symbolized so much more. This is one of the greatest upsets of the decade not simply because Sampras was favored, but because of everything that followed. Sampras would retire in two years and Federer would eventually live up to those wild expectations. And forget about Sampras getting any revenge – the two would never again face each other on the professional level. – Christopher Glotfelty

9. Edmonton upsets Detroit in 2006 Stanley Cup Playoffs

Detroit was a heavy favorite in the quarterfinals, as the top-seeded Red Wings were coming off a terrific 124-point regular season in which they captured the President’s Trophy. Meanwhile, the Oilers squeaked into the playoffs as an #8-seed after a 95-point regular season. The Red Wings won Game 1 in Detroit, but dropped Game 2. The two teams also split the next two games in Edmonton. The Oilers then closed out the series winning Game 5 in Detroit and Game 6 at home, both by one-goal margins. The series featured two double-overtime games (Game 1 & Game 6) and all six games were decided by two goals or less. – John Paulsen

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