Well Ryo's strongest environment kills them all. Being a volcano type area and all that so he auto wins everytime. (unless you count the anime when Sasuke's katon that hits Naruto melts rock into magma and Naruto is all fine but that's just filer of that VoTe fight)
Rowen/Touma's element is space so again if he was in an environment that suited him they all die.
Cye/Shin I guess best place would be the Rain Village so depends on who he faces really. But he's going to be mowing over fodder, and genin, and chunnin like they were nothing. If the likes of any of the Hokages, Raikage, or Killer Bee it may not be easy.
Kento/Shuu is stronger than anybody in Naruto, has the speed to keep up with anybody in Naruto, but is extremely dumb. Any genjutsu user, or even Shikamaru or Shikaku face him he's beaten.
Sage/Seiji is probably, well not the smartest but the most suited to fight genjutsu users, while being among one of the smartest (Rowen might be smarter but he's more book smart when Sage is more strategic/fighting smart) when it comes down to it. Where Cye is more of a pacifist, and will fight if needs to, and Kento is dumb, Sage has been training by a strict grandfather since he was really young so unless he's up against Itachi, or perhaps even Sasuke he mows down pretty much anybody.
Anubis/Sh'ten pretty much just rapes whoever he's up against. Excluding Madara, Yondy and Pein. As his whole Quake with Fear isn't going to be trapping them.
In scenario two depends on who goes first. Though Ryo or Rowen stop everybody when it gets moved to there environment. And I'm assuming Ryo can't use his Inferno Armor.