The Creeper of Jeeperscreepers Davy Jones of POTC
Scenario one
Top of Davy Jones ship 24 yards Away is the chest that has Davy Jones heart.
The creeper has his battle axe while the Davy Jones has his one sword he used in the last battle before he was killed.
If the creeper stabs Jones heart he wins, or if he's able to knock out Davy Jones.
If Jones can kill the creeper in some way on his own then he wins, or if the creeper retreats by flying off and away from the ship.
The kraken can't be used to help Davy Jones.
Scenario two
The Golden Gate Bridge San Francisco California
The loser is the one the one that gets knocked off the Golden Gate Bridge falling to the bottom. The creeper can't use flying he has his battle axe while Davy Jones has the same sword he used in the final battle.
Again the kraken can't be used to help Davy Jones.