Round one, Matt stomps. Hell's Kitchen is where he grew up, he has every advantage there. Tim's flight and armor shouldn't even be an issue.
Round two, Matt wins. Tim's got some limited knowledge of the area while Matt's got none. It isn't a big enough advantage to change the outcome of the battle but it's good enough to give Tim a good shot considering he has better maneuvering opportunities. Matt would only have to worry about gadgets here but since we haven't seen too many from Tim and Matt can evade them since there's still open space, it shouldn't be a problem.
Round three, Tim barely wins. Arkham isn't exactly somewhere I'd imagine Tim being too familiar with, but he knows it enough to have that advantage over Matt along with the fact that it is packed with rowdy inmates which won't help Matt's senses. It's not necessarily enclosed but it's just open enough to give Tim limited flight maneuverability, Matt's biggest problem is the inmates and Tim is known as the best detective of the Robins so he will notice after a little bit of observation that Matt is extremely sound sensitive. This bit of obvious info should give Tim the idea of relying on the inmates loud and obnoxious behavior to cover himself, what he may not be counting on is the inmates collective sounds bouncing off of every surface and mapping out the whole environment for Matt. This is only a limited advantage as that much noise would make it hard to concentrate on a single target since it is all different kinds of sound coming from all angles hitting everything at once, this is what Tim has to count on to even the odds. I think the Red Robin Armor is more durable than the Daredevil suit (especially the wings which are made of Inertrite) and it would help him against nerve strikes, evening the odds further. If the OP means no equipment as in no gear, gadgets, weapons or suits .... then Matt wins with some difficulty since Tim has no protection and no flight advantage (but then, what would they otherwise be wearing?). If they get to keep their suits on then Tim wins since his flight, armor, and razor sharp Inertrite wings are a bit of an advantage. Not to say Matt doesn't completely outclass him in every physical area such as strength, agility and skill, but if Tim takes advantage of the inmates and his wings blades then he cut his path to victory and earn himself a few broken bones.
Now that the OP has been edited to something that isn't a complete rapestomp and now allows gear, Tim can use gas pellets to immobilize Matt since the area they are in is somewhat enclosed and the gas can spread without thinning out too much and will still effect Matt over time. Tim's regular projectiles and melee attacks won't be of much use since Matt still has the edge of reaction speed, skill and agility and would chump Tim if he got too close. A gas pellet to mess with Matt's nervous system would do well enough although he isn't going down after that, it will make attacking physically and with projectiles more possible and may grant Tim the chance he needs to win here.
Matt wins 2/3...at least Tim doesn't go out like a defenseless baby this time....
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