Usually means: Endgame move securing chess win.
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We found 11 dictionaries that define the word checkmates:

General (9 matching dictionaries)
  1. checkmates: Merriam-Webster
  2. checkmates: Collins English Dictionary
  3. checkmates: Vocabulary.com
  4. Checkmates, checkmates: Wordnik
  5. checkmates: Cambridge Advanced Learner's Dictionary
  6. checkmates: Wiktionary
  7. checkmates: Dictionary.com
  8. Checkmates, The Checkmates: Wikipedia, the Free Encyclopedia
  9. checkmates: TheFreeDictionary.com

Business (1 matching dictionary)
  1. checkmates: Legal dictionary

Computing (1 matching dictionary)
  1. checkmates: Encyclopedia

(Note: See checkmate as well.)

Definitions from Wiktionary (checkmate)

noun:  The conclusive victory in a game of chess that occurs when an opponent's king is threatened with unavoidable capture.
noun:  (figuratively, by extension) Any losing situation with no escape; utter defeat.
verb:  (transitive, chess) To put the king of an opponent into checkmate.
verb:  (transitive, by extension) To place in a losing situation that has no escape.
▸ Also see checkmate





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