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All answers having "Penniless" as clue:

4 Character Answers:

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POOR



5 Character Answers:

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BROKE

NEEDY

SKINT



8 Character Answers:

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BANKRUPT

DIRTPOOR

INDIGENT

STRAPPED



9 Character Answers:

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DESTITUTE

FLATBROKE



10 Character Answers:

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BUSTEDFLAT

STONYBROKE



11 Character Answers:

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IMPECUNIOUS