Entry 1 sense Webster, 1913 Checkerboard /(chĕk"ẽr*bōrd`)/ · Check·er·board · IPA /ˈt͡ʃɛkɚˌbɔɹd/ 01 n. A board with sixty-four squares of alternate color, used for playing checkers, chess, or draughts. 1. A board with sixty-four squares of alternate color, used for playing checkers, chess, or draughts.