in 1900, Tottenham won the Southern League title and crowned this achievement the next year by winning the FA Cup (1901). so you could say 1900 but this was an amature (semi-pro) league so many people state it as 1901 being the year we first won a cup.
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The Hart Memorial Trophy was first won by Frank Nighbor of the Ottawa Senators after the 1923-1924 season.
Chris Chelios in 1996
Paul Hornung was the 1956 Heisman Trophy winner who played on a Notre Dame team that finished the season 2-8. He is the only player from a losing team to win the Heisman Trophy.
The Heisman Trophy
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