Multiple Man would eventually win. Wolverine couldn't handle a large amount of trained fighters on him at once, all thinking with the SAME brain. It'll be too much for him. Especially since Jamie can really just keep going.
The problem would be that MM doesn't start off with a clone army, it's kinetic energy that triggers the duplication, and if wolverine was going for a kill shot it wouldn't just be a bludgeoning hit. . .
Multiple Man doesn't like killing (he was shaken up badly when he killed Melloncamp). Also, his dupes don't consider themselves cannon fodder, so if the fight is based on the direct approach, Wolverine wins (some of the dupes might actually side with Wolverine in the fight). Put the environment factor in, then Multiple Man could come up with something to take him down (if the dupes are compliant).
Well actually he wasnt shaken up. He killed Melloncamp all instinctively. It was his other dupe who was shaken up. I tend to dissagree with you a bit. If he knows he and Wolvie are about to fight, his frame of mind is totally different. Hes actually thinking of ways to beat logan. Therefore the dupes that come out are going to help him most likely. Even if there are 1 or 2 that wont help him(which i doubt), Jamie can just absorb them back and make more.
In the Madrox series, he states..."Nice to know that in times of stress, im producing dupes who are automatically helping me instead of second-guessing me or trying to kill me." "Maybe its because im so focused on escaping." Thus, if hes focused on beating Wolverine, the dupes will help him.