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Roland is far more skilled in combat and has had plenty of experience dealing with threats of Jason's caliber and higher. He's also dealt with illusions before, and while he can't actually see through them (and indeed has a spotty track record as far as they are concerned), I wouldn't say Jason's are all that notable in comparison to what regularly shows up in DT's setting.
However, the main problem is that I'm not sure if Roland can put him down for good. His raw durability is at least as high as the Gunslinger's (which is no small thing at this tier), and the guy instantly regenerated from having a grenade obliterate most of his torso. Roland's guns are stupid strong and would undoubtedly tear Jason apart, but I'm not certain whether or not that would be enough to close things out.
If Roland can get past the healing factor, then I'm pretty sure he wins. But if not, Jason eventually just muscles his way through the damage until he has an opportunity to get up close and personal.