Entry 2 senses Webster, 1913 Checkered /(chĕk"ẽrd)/ · Check·ered · IPA /tʃˈɛkərd/ 01 a. Marked with alternate squares or checks of different color or material. 1. Marked with alternate squares or checks of different color or material. “Dancing in the checkered shade.” — Milton. 2. Diversified or variegated in a marked manner, as in appearance, character, circumstances, etc.; as, a character with a checkered past “This checkered narrative.” — Macaulay.