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The Headless Horseman vs Jack Sparrow

Scenario 1 - Sword fight, The Horseman get's his sword and axe and can be killed.

Scenario 2 - Jack has to survive for 60min, Immortal Horseman Vs jack on the Dutchman During the battle between the Brethren court and the east India company.

Scenario 3 - The same as two except Jack also has to protect Elizabeth.

Who wins?

Jack in all three. He has way too much luck to lose here. He'd probably end up accidently knocking the Horseman overboard in 2 and 3.