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Alright he is healed to 100% after every fight. Also he becomes a master at using the adamantium/Vibranium shield. Delroy gets prep on each fighter to see what he is up against.

Captain America(Delroy Garrent Jr)
http://marvel.wikia.com/wiki/Delroy_Garrett_Jr._%28Earth-616%29

1.Daredevil
2.Batman
3.Deadpool(K.O wins the fight)
4.Deathstroke same as 3
5.Wolverine same as 3 & 4
6.Spider-Man/no webbing

Cap clears it

stops at 3, if by some chance he makes it past wade, wolverine guts him!