Its a 50/50 IMO. Madara is smarter and has the full power of rinnegan, while obito is stronger overall, madara is more experienced and can pretty much counter all juubito's moves
- IT aint working on madara cus rinnegan
- madara with a rikudou/sage mode enhanced PS is gonna cut the tree in half
- he has rikudou chakra so his attacks won't be negated and he can touch tsb
- he is fast enough to fight on par
- he can escape the barrier and quad juubi dama by projecting limbo outside the barrier and switching with it
He pretty much counters errthing
So IMO its 50/50, madara has a higher chance of winning IMo though