If in real world it doesn't seems to be a real fight too. In real world mister anderson could easily beaten by a rough guy. Are u count that as a real fight?
If Superman go into the matrix world, it means he is plugged into the system... so if he can win or not is depends whether he can free his mind or not.
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Superman has his powers all the time. Most of Neo's powers only happen in the Matrix. Besides, Neo can't burn things with his eyes and he can't see through things in real life. He can only do a couple of things outside the matrix.
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I am the Dark Side~ Sig image by Tracyn
That's a given. Superman. Superman won't have much trouble freeing his mind to fly, be superstrong and use all his other abilities in the Matrix because he already knows and believes he can. Neo had trouble before because he was only human and had trouble accepting the fact that he could be a battery full of controllable energy. If Supes frees his mind, he can have more powers. Besides according to the enter the Matrix game, you only have a certain amount of focu which lets you slow things down, Superman can do that forever if he wants and Neo wouldn't be able to doge his attacks since Supe is faster than a speeding bullet.