Obito - Minato(FTG), Tobirama(FTG), Bee(hachibi mode), Naruto(Kurama mode), Kakashi(kamui), Sasuke(amaterasu), Ay(V2), Oonoki,(Lightening people for speed), mei( Mist to hinder his visual prowess)
Madara - Hashirama(Mokuton), Hiruzen(enma pole), Tsunade(dat power), Sakura(dat power), Guy(gates), Gaara(Sand for defence and to **** with him)
Personally, I believe only Speed demons can take on obito because they need to exploit kamui with extremely quick attacks. Bee and narruto would be useful for chakra boosts and protection from his jin upgrades as with primary speed attacks.
Whereas, People who use alot of attack that don't use chakra are needed for madara. Madara has already shown that the only way you're hitting him is if you use physical force.