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All answers having "Gamble" as clue:

3 Character Answers:

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BET



4 Character Answers:

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DARE

PUNT

RISK



5 Character Answers:

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STAKE

WAGER



8 Character Answers:

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CHANCEIT

MAKEABET

RUNARISK



9 Character Answers:

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CRAPSHOOT

TAKERISKS

UPTHEANTE



11 Character Answers:

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TAKEACHANCE