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All answers having "Miserable" as clue:

5 Character Answers:

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DEPTH

LOUSY



6 Character Answers:

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ABJECT

EXEMPT

WOEFUL



7 Character Answers:

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DOLEFUL

FORLORN

HELLISH

PITIFUL

SQUALID

UNHAPPY



8 Character Answers:

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APOSTLES

DOGSLIFE

WRETCHED



9 Character Answers:

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WOEBEGONE