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Cupset refers to a situation in a sporting competition (typically where a Cup is the top prize to be awarded) where a team from a lower league defeats a team from a higher league.

Severity ranges from "Minor Cupset" (i.e. a team beating another in the division above), "Major Cupset" (i.e. a team defeating another two or three divisions above them), to "Miraculous Cupset" (i.e. a team that isn't even a part of the 'official' league(s), defeats a team in the top divisions of the official league(s).)

"Cupset" is a contraction of the words "Cup Upset". It derives from the popular FA Cup Competition run by the Football Association for English football clubs, but can theoretically be used for any competition with similar league styles.
"Do you remember when Southend United beat Manchester United in the League Cup? What a cupset that was."

"As it stands, it's Liverpool nil, Stevenage one, and with only five minutes to play, Liverpool are looking at a major cupset."
by Stuart Robbins January 05, 2008
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2
when an underdog team faces a much better team in a cup competition and defeats the odds to win

first coined by the BBC sport website on 5/1/08
"Non-League Chasetown are looking to provide the cupset of the day against Championship side Cardiff"
by cs192 January 05, 2008
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3
Footballing occurrence in a cup competition where a team placed significantly lower down in the football league overcomes all odds and defeats the higher-ranked side.
Oldham are 1-0 up on Everton, we definitely have a cupset on our hands!
by Gilldrew Anespie January 12, 2008
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4
A result in a Football (Soccer) match which sees a distinctly better team lose to one that is in a lower division. This applies only to knockout competitions, and in particular, The FA Cup.
The word was invented on January 5th 2008 by BBC Sports Correspondent Caroline Cheese, and introduced to the 606 community.
I can't believe Chasetown are beating Cardiff! We might see a cupset here!
by Stanley484 January 05, 2008
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5
A cupset is another way of saying "Cup Upset", which is when a small team (usuall non-league) manages to defeat a very large team (usually in the English Premier League, Championship, League 1 or 2) to go to the next round of a competition. Usually refers to the FA Cup (football)
Chasetown will be hoping for a 'cupset' today as they take on Cardiff in the FA Cup.
by Atashe'Gol January 05, 2008
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6
An unexpected win in any football cup tie
Shrewsbury FC knocking Everton FC in the 2002-03 season FA cup third round at Gay Meadow. Therefore, a cupset.
by Alexc567 January 05, 2008
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