Might mean (unverified): Unexpected victory by weaker team.
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We found 2 dictionaries that define the word cupset:

General (1 matching dictionary)
  1. cupset: Wiktionary

Slang (1 matching dictionary)
  1. Cupset: Urban Dictionary

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Definitions from Wiktionary (cupset)

▸ noun:  (sports, British, slang) An upset in a Cup competition.

Similar:
cup tie, upset, cupper, Cup Final, cush, cockmatch, cup check, mug-hunting, fixture, break, more...

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▸ Popular adjectives describing cupset

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Similar:
cup tie, upset, cupper, Cup Final, cush, cockmatch, cup check, mug-hunting, fixture, break, more...



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