Crossword clues for the word: HEADLESS The word HEADLESS has appeared as an answer to at least 7 crossword clues on different crossword puzzles. Crossword clues for HEADLESS Showing 1 to 7 of 7 results Clue(s) Having lost leader, get sealed somehow inside high school Like a literary horseman Like an Irving horseman Like Irving’s Hessian horseman Like Irving's horseman Like the horseman of Sleepy Hollow. Word associated with Sleepy Hollow