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Owlman is the evil version of Batman? who wins when he faces off against Batgirl.

Batgirl baring prep.

As discussed in Trinity, because the CSA offs all it's foes it has a bit less experience due to lack of repeat villains, and Cass is already a bit better than Batman in HtH.

Cassie should be able to "read" Owlman and defeat him 8/10


unless of course this is Stephanie Brown in which case Owlman beats her

Assuming this is Cassie she wins.