Story: Malebolgia sends Al Simmons/Spawn to Earth and Spawn's mission is to kill Deadpool for Wanda's life. Spawn encounter Deadpool and Wade Wilson/Deadpool has nothing to do with everything and everybody. Also, Deadpool must fight with Spawn at night time. If Spawn fails, Malebolgia will send him back to hell and he will be kill by Malebolgia and the rest of the Spawn Hell's Army.
Who would win and why?
I'll say Spawn.
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Verified answer
Defintiely Spawn. Deadpool is not even in the same league as Spawn. Spawn can only be defeated by magical weapons. Deadpool has none.
Quite some time back, Marvel and DC had a few crossovers, and one of them was Deadpool and Deathstroke.
Technically, Deathstroke won, but Deadpool was given the victory.
The reason is simple, and would be why Deadpool would also win out over Spawn.
Although Deathstroke was the far superior fighter, nothing he could ever do actually finish Deadpool off because of his healing factor. He would keep healing, and would keep getting back up, and would not shut up. So in the end, Deathstroke just walked away to get away from him.
The same would happen with Spawn I think.
Spawn. He can't kill Deadpool, but he can hurt him.