If this fight were to take place, I fully admit that Deathstroke is not only more skilled, but he's also smarter, he's stronger, and he's got better reflexes than Deadpool, so those are his advantages.
Deadpool's advantages are his advanced healing factor, his speed-via teleporter-his unpredictability, and his arsenal.
Now, in a straight-up sparring match you might think Deathstroke would have the advantage because he's more skilled, but he wouldn't. Deathstroke fights by predicting his opponent, he fights by playing his enemy like a chess master, he can't do that with Deadpool. Deadpool is simply that unpredictable and his teleporter only makes him that much more so. He would be nearly impossible to hit, and then when he did get hit, Deadpool would not only feel no pain, but he would be able to heal right back from any hit, meanwhile while Deathstroke has a limited healing factor, it's nowhere near as fast or effective as Deadpool's.
People will bring up Deathstroke's armor, but Deadpool's swords are a knock-off of Adamantium, allowing them to cut through almost anything. Even if he didn't use his swords, there are plenty of places Deathstroke is not armored, and if there weren't, the armor he wears would likely break down after a relentless assault from Deadpool's arsenal. It's just gonna come down to Deathstroke cannot hit Deadpool at all, he can't predict what Deadpool is gonna do, and that handicaps Deathstroke entirely.
This winner is Deadpool for his sheer unpredictability.
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