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All answers having "Winner" as clue:

3 Character Answers:

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ACE



4 Character Answers:

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ELKE



5 Character Answers:

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CHAMP



6 Character Answers:

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SHOOIN

TOPDOG

VICTOR



7 Character Answers:

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BESTMAN

PRETEND

SERIPAK

TAKEALL



8 Character Answers:

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TAKESALL



9 Character Answers:

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BETSYKING

MEGMALLON

TOPSCORER



10 Character Answers:

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BESTOFSHOW

ROYALFLUSH



13 Character Answers:

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KINGOFTHEHILL



15 Character Answers:

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ANNIKASORENSTAM

LOTTERYCLAIMANT