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Imo Matt takes this rather easily. Not only he is a higher end of Large Star level, but insta-kill attacks take care of Dave's clones, the only way I can see Dave winning is if he starts by going back in time to kill a weaker Matt.
Iirc, Dave doesn't like to use his time powers very much, though he did do so when forced into a corner, such as when he, Dirk, and Terezi fought Alpha Jack.