Usually means: Expert player skilled in chess.
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We found 4 dictionaries that define the word chessmaster:

General (3 matching dictionaries)
  1. Chessmaster, chessmaster: Wordnik
  2. chessmaster: Wiktionary
  3. Chessmaster: Wikipedia, the Free Encyclopedia

Sports (1 matching dictionary)
  1. Chessmaster: Chess Dictionary

Definitions from Wiktionary (Chessmaster)

noun:  Alternative form of chess master [An exceptionally skillful chess player, especially one who has won a major competition.]

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