Obito controlled the most at once, but he had additional tools(chains + edos already being subdued) to help him throughout it, so I'll just discredit that. From what I've seen, all of them are perfectly capable of trancing Kurama without any real difficulty. The fact honestly eliminates any real genjutsu feat to decide this aside from Sasuke's Rinnesharingan glance.
Other than that, Obito had difficulty keeping the Juubi under control at first while Madara hadn't encountered that problem despite hosting more Juubi chakra than Obito did. Sasuke didn't bother hosting them at all, so he can't really be compared in this one just as those two couldn't be in the last.
I'll put my bets on Sasuke though. His genjutsu skill itself(not sharingan genjutsu, his literal skill with genjutsu) was never described as great, but the Rinnesharingan seems to have amped up his genjutsu to the point where just a glance is enough to trap multiple beasts. Clearly the eye comes with insane genjutsu capabilities & these Rikudo powerups often outshine actual talent.