-Obito will be forced to fight Kakashi, and then he beats him.
-KCM Naruto and Sasuke might fight, and Sasuke would beat him in that match.
-Orochimaru and Jiraiya would fight, and Jiraiya would beat him as long as he made it in Sage Mode, which should easily happen if Naruto supports him with clones. He can do it on his own anyway.
If Naruto has been killed before Orochimaru has been killed, Sasuke one shots Jiraiya. Even if Naruto hasn't been killed Jiraiya can't even do anything significant to Sasuke. Amaterasu or Susanoo Arrow would one shot him. Naruto's offense is negated by Amaterasu/Enton, and he's eventually mowed down by Susanoo+Sharingan precognition.
So Team 1 wins if Obito can get to help Sasuke before Naruto is killed. Team 2 might win if Naruto is killed by Sasuke before Obito can beat Kakashi and come help. The first scenario happening is more likely since Naruto isn't going to last long in close combat against a Susanoo used by a guy who can already react just as fast he can with a Susanoo that is >>>the user in close combat and can pretty much tank or outright negate any offense Naruto throws at it. Not to mention he can just start spamming black flame to prep Kirin.
Once Nardo has bitten the dust, Jiraiya gets smitten, then it's Obito vs. Sasuke. Obito trying to warp Sasuke will only result in him spawning Susanoo and crushing Obito. His offense is useless, so is Genjutsu. So unless he just runs the whole match, he loses. If he does, he outlasts and Sasuke dies, then team 1 would win.