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Well both seem to have type 8 immortality so winning by death is not an option

I'd be more inclined to say Dwight wins due to better arsenal which will let him incap quicker Plus his luck could help him, tho I don't know how potent it is
 
also Dwight's weakness is that without his glasses, He cannot see, so all SCP-049 has to do is take off the glasses, and he basically wins.
 
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