Crossword clues for the word: DOLEFUL The word DOLEFUL has appeared as an answer to at least 8 crossword clues on different crossword puzzles. Crossword clues for DOLEFUL Showing 1 to 8 of 8 results Clue(s) Causing grief Dreary Fed up with poor pay? Joyless Melancholy Sad although loaded with benefit money? Sad, though loaded with unearned income? Unhappy though generously benefited?