I would generally pick Iron Man because Tony Stark and Bruce Wayne have similar intelligence plus Tony has a super-powered suit. However, since Batman has no powers I think Iron Man won't take him seriously and some accurately placed Batarangs on that suit and it will be Tony Stark, not Iron Man, dealing with Batman.
Batman wins.




LONG LIVE LOU SCHEIMER!!!
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Besides, if I worry about matching characters with similar powers and/or costumes, I end up with Batman VS Moon Knight and Superman VS Hyperion. At least I know Batman & Iron Man both have a lot of fans.

