Considering we're not talking about juubi jin Madara and Obito.
We've never seen Obito in his prime. He never had access to all his MS power due to having only one of his sharingans, still his kamui was one the best doujutsus in NV and he was able to deal with almost any shinobi relying only upon that. If its a fight all at once among the four I think adult Naruto and Sasuke would come on top. Madara was over hyped imo. Hashi era Madara would lose to both Sasuke and Naruto and then both of there fight would end up in a draw again.