Spider-Man's spider-sense and superior speed make Deadpool's healing factor irrelevant if he can't land a hit.
On paper, this looks closer than it actually is. Deadpool is a phenomenal combatant with master-level proficiency in virtually every weapon known to man, and his healing factor means Spider-Man literally cannot put him down for good. But Spider-Man doesn't need to kill Deadpool โ he just needs to win.
Spider-Man's spider-sense is the ultimate counter to Deadpool's fighting style. Wade relies heavily on unpredictability, fourth-wall breaks, and chaotic combat to throw opponents off. But Peter's precognitive danger sense doesn't care about psychological warfare โ it reads the physical threat and reacts before Deadpool even commits to an action. Add in Spidey's vastly superior speed, proportional spider-strength (he can lift about 10 tons), and his webbing which can immobilize Deadpool completely, and Peter has all the tools.
Deadpool's healing factor is formidable, but it's not a win condition against someone who can web him up, hang him from a skyscraper, and walk away. They've fought multiple times in the comics, and Spider-Man consistently has the edge in direct combat.
Deadpool's healing factor means he physically cannot lose by attrition โ he will always get back up. His centuries of combat experience and willingness to use lethal force (guns, swords, explosives) gives him options Spider-Man doesn't have. If he can get past the spider-sense through sheer chaos, one clean katana strike could change everything. Plus, Deadpool fights dirty in ways Peter's moral code won't allow him to counter.
Spider-Man is faster, stronger, and has precognition. His web-shooters can immobilize Deadpool completely, and his agility means Wade's bullets and blades rarely find their mark. In their comic encounters, Peter consistently dominates the hand-to-hand exchange. Spider-Man is also significantly smarter than Deadpool and can use the environment to his advantage โ fighting near buildings plays perfectly to Spidey's movement style.
Spider-Man wins the fight, but can't truly finish Deadpool. In a straight battle, Peter's superior stats across the board let him control the encounter from start to finish. Deadpool would eventually regenerate, crack a joke about being beaten by a teenager, and probably suggest they get tacos instead.
Deadpool also fights
Spider-Man also fights