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All answers having "Destitute" as clue:

4 Character Answers:

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POOR



5 Character Answers:

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BROKE

NEEDY



6 Character Answers:

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BADOFF

INNEED

INWANT



8 Character Answers:

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BANKRUPT



9 Character Answers:

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FLATBROKE

PENNILESS



10 Character Answers:

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DOWNANDOUT