1906 - The Chicago White Sox over the Chicago Cubs. The Cubs won 116 games that season and still hold the MLB record for season's winning percentage. The White Sox won 93 games.
1924 - The Washington Nationals over the New York Giants. The Giants were in their fourth consecutive World Series. The perenially losing Nats were in their first ever. Two bad hop singles and a catcher stepping in his face mask and dropping a foul ball allowed the Nats to win Game 7.
1969 - The New York Mets over the Baltimore Orioles. The Orioles won 109 games that season.
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2004 NBA Finals. Detroit Pistons trouncing the Los Angeles Lakers. The Lakers had Kobe, Shaq, Karl Malone and Gary Payton. The Pistons beat them in 5 games. 3 of their 4 wins were won by 12 pts or more. The only game the Lakers won was because of a last second 3-pointer by Kobe. The Lakers were supposedly "unbeatable." They were beaten badly and were so embarrassed they completely dismantled the team the following year. This is the biggest, most underrated upset of all time.