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All answers having "Skipper" as clue:

3 Character Answers:

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SIS



6 Character Answers:

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TRUANT



7 Character Answers:

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BOATMAN

CAPTAIN



8 Character Answers:

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THROSTLE



10 Character Answers:

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SEACAPTAIN

SHIPMASTER



11 Character Answers:

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BOATCAPTAIN



15 Character Answers:

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AIRPLANECAPTAIN

GILLIGANSFRIEND