I liked Deathpol, wich they'd bring him back in DC with 4 or 5 monthly titles and miniseries.
Anyway, they can win via immobilization with concrete foam and things like that but otherwise deathpool probably wins, no matter how much damage he took, it didnt even slow him down, Deadpool's functioning efficiency decreases while his body recovers from very serious wounds, specially to the brain, but Deadpool's damage soak seemed limitless.