Pilot of Gurren
Agent Carolina vs Master Chief
Agent Carolina (from Red vs Blue Seasons 9 and 10) versus Master Chief (using his armor from Halo 4).
For the sake of conflict, include Master Chief's military career from the Halo Expanded Universe.
Before they fight, whose marksmanship is better?
And then during the inevitable fight, which super soldier will beat the crap out of the other?
Well Halo 4 hasn't come out yet, so there really isn't much in the way of feats for the suit.. But if by Military Career, you mean his feats in combat from the EU, he won't need it. The Mark V and Mark VI variants will be more than enough to let him tear Carolina to pieces.