Round 1: The weird part about this is, these fights take place in a context that DD would never be in. He'd never be fooled by any of the illusions, and therefore would have caught on to Mysterio and never have let his guard down in the first place. However, even if you just literally just drop DD into the fight right before the trainyard, I still think he gets the jump on Mysterio by knowing exactly where he is and taking him out before Mysterio can adjust and issue a kill order. At that point, he didn't have the entire Stark Fleet of drones dispatched (they come out for London), so DD wouldn't have to deal with nearly as many.
Round 2: Dropping him in right before the battle of London is too much for DD to handle, he gets overwhelmed by the sheer firepower and protection that Mysterio has for himself. But again, this is putting a character in a situation that they wouldn't have let themselves get into.
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