It's close, but I think that this fight goes to Raphael. He trumps Robin on physical stats (though I feel as though some people may be exaggerating his capabilities) and is at least on par with his skill, if not better. Robin is better equipped and likely smarter and a better tactician, but people are discounting some of Raph's gear. He's been shown to carry shuriken and other throwing weapons, making the separation they start at less of a factor. Can Raph hit Robin? Probably not. But, he can put enough pressure on him to close the distance, where he can hit him.
Both characters are used to fighting as a team, but both also have experience at lone combat particularly given that this is IDW Raphael who was separated from his brothers for a considerable amount of time in the beginning. I feel, in general, Damian fights lower-tier foes in terms of skill, while Raph is more used to fighting higher level combatants. Where Raph is fighting the Foot, Damian's beating up simple thugs, the likes of which the Foot have been shown to be able to stomp. This doesn't diminish Damian's capabilities, but it does make Raph more used to tougher foes.
So, as I said, Raphael takes this fight, but not easily. He'd probably start off going easy on Damian until the kid did something to prove that he shouldn't and then it would devolve into something of a brawl with Damian liking trying to break contact and Raphael doggedly pursuing.
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