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Round 1: In NYC.

Round 2: No top of a moving train.

Round 3: In a jungle with prep.

Standard equipment for all rounds.

Who take it?

crossbones in 1 and 3, he even gives Cap problems.

Crossbones breaks Grayson Bane-style, or gives him the Face Beam of Death.

1- Dick
2- Dick
3- Crossbones

I think that the aerials abilities and gadgets of Dick will help him a lot in the 2 first scenarios. Crossbones is a soldier, the 3rd fight is taylormade for him.

Grayson is a good match against Crossbones, agility goes a long way. In the last one, however, he will lose.

Batroc would be a better match for Grayson, he's got enough agility and mobility to take him on his own game.