Cap is the better fighter, but Deadpool's healing factor makes it impossible to finish him.
In terms of pure combat skill, Captain America is arguably superior โ better technique, better tactical mind, and the vibranium shield gives him an incredible edge. But Deadpool can't die.
Cap could 'win' the fight a dozen times โ knock Deadpool unconscious, break bones, deliver shield strikes that would kill anyone else. But Wade keeps getting up, regenerating, and coming back with another quip.
This is the classic 'attrition vs. skill' matchup. Cap can win every exchange but can't deliver a permanent victory. Deadpool can lose every exchange but will eventually outlast Cap's stamina.
Cap's shield is key โ it's one of the few weapons that Deadpool's healing factor can't help with, since vibranium strikes could theoretically keep Wade down. But Cap's human stamina means he eventually tires while Deadpool's healing factor means infinite endurance.
Cap is the superior tactical fighter with a vibranium shield that can keep Deadpool down. His combat skill and leadership experience give him an edge in the actual fighting. Cap has fought and defeated enhanced individuals through superior strategy.
Deadpool can't die. Cap eventually tires. That's the entire argument, and it's sufficient. Wade's weapons are also more lethal than Cap's โ katanas and guns versus a shield and fists.
Deadpool wins through attrition. Cap dominates the actual fighting, but he can't permanently put Deadpool down, and his human stamina has limits that Wade's healing factor doesn't share.
Captain America also fights
Deadpool also fights