Madara (Rinnegan)
Sasuke (Rinnegan adult)
Naruto (Adult)
Obito (dual MS)
Then either sasuke or naruto wins depending on how the other fights. Naruto and Sasuke low diff any version of madara that isn't juubi jin. As for Obito only Sasuke would have an eaay time because he could just link upbwith the kumai dimension and it would make the fight significantly easier. For naruto it would be tricky as he can't really hit Obito for five minutes. But obito can't really fatally injur naruto either