mid-13c., "game of chess (or checkers);" c. 1300, "a chessboard, board with 64 squares for playing chess or similar games; a set of chessmen" (all now obsolete), a shortening of Old French eschequier "chessboard; a game of chess" (Modern French échiquier), from Medieval Latin scaccarium "chess-board" (see check (n.1)).
The meaning "pattern of squares" is from late 14c. That of "a man or piece in the game of checkers" is from 1864. British prefers chequer. From late 14c. as "a checked design." The word had earlier senses of "table covered with checked cloth for counting" (late 12c. in Anglo-Latin), a sense also in Old French (see checker (n.2)).
"table covered with a checked cloth," specialized sense of checker (n.1), late 14c. (in Anglo-Latin from c. 1300); especially a table for counting money or keeping accounts (revenue reckoned with counters); later extended to "the fiscal department of the English Crown; the Exchequer" (mid-14c.; in Anglo-Latin from late 12c.).
"one who checks or controls," especially "one who collects money for others," 1867, agent noun from check (v.2).
"pattern of squares in alternating colors," c. 1400, short for checker (n.1). As a fabric having such a pattern from 1610s.
late 14c., "marked with squares or checks," past-participle adjective from checker (v.). Checkered past (1831) is from a figurative use: "variegated with different qualities or events, having a character both good and bad."
c. 1300, "a chessboard, checkerboard," from Anglo-French escheker "a chessboard," from Old French eschequier, from Medieval Latin scaccarium "chess board" (see check (n.1); also see checker (n.2)). The governmental sense of "department of the royal household concerned with the receipt, custody, and disbursement of revenue and with judicial determination of certain causes affecting crown revenues" began under the Norman kings of England and refers to a cloth divided in squares that covered a table on which accounts of revenue were reckoned by using counters, and which reminded people of a chess board. Respelled with an -x- based on the mistaken belief that it originally was a Latin ex- word.