I would go with Kirk because the TC didn't specify Starship combat alone. I'm looking at this in a bit more of a broad way.
To me it seemed that Kirk was presented with the widest range of bizarre and seemingly unwinnable situations by far. Many times he was forced to confront godlike beings and species with tech far beyond his own. All of the Captains did, but they all relied much more on their subordinates to supply them with options. Kirk occasionally did as well, but many times he simply tricked or out thought enemies that he would normally have had no chance to beat.