Suggested by Destroyer Jack Sparrow is an immortal pirate with years of experience under his belt. The guy may be treated like a joke most of the time and he’s not particularly likable but he can fight. If Derpy gets in close then Jack will finish her off with his sword and if she stays afar then he’ll pull out the ole gun. Either way I don’t see many chances for her here and Jack has a lot of time on his side with his increased durability. Jack Sparrow wins.