Crossword clues for the word: PENNILESS The word PENNILESS has appeared as an answer to at least 7 crossword clues on different crossword puzzles. Crossword clues for PENNILESS Showing 1 to 7 of 7 results Clue(s) Broke Flat broke Poor writer on 13's river boat River's entering farm structures, leaving you poor See 60-Across Simple Simon's status. Very poor