<p>Madara vs Kaguya: Kaguya wins, unless Madara attains both six path yin and yang powers, like Hagoromo somehow could <i>(after all, Madara had almost Hagoromo's power</i>), and I’m not even sure if whether one person has both powers, can they seal Kaguya, or two persons are needed to use the powers individually...or unless Madara knows/creates some other method of sealing Kaguya
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Madara vs. Hagoromo/Hamura: Madara has a chance to win, as even though Hagoromo and Hamura possibly have had more chakra and also some great/unique techniques <i>(not necessarily offensive /defensive techniques)</i>, they were more of sages than shinobis and they existed at a time when ninjutsu was much less developed <i>(though they battled TT and sealed Kaguya together)</i>. Madara was born at a time <i>(a competitive and warring era, where individuals strived to hone their skills and battle for glory)</i> when ninjutsu was vastly developed, was decently trained, had seen and participated in a great deal of wars and battled with great shinobis gaining practical/public/secret knowledge and strategic and tactical warfare experience - not to mention, at his peak, his power level was almost at par with Hagoromo's. At his peak, he has a chance of beating them one on one
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Madara vs. Naruto/Sasuke: Madara himself claimed that even with Naruto & Sasuke receiving six path powers, he had both of theirs power combined <i>(while we do not have to necessarily take him at his word literally, but he was right to a certain extent)</i>. While battling both of them <i>(included being also attacked/distracted in between by other shinobis)</i>, Madara was more concerned with activating mugen tsukuyomi than killing them, and after he obtained both rinnegan + absorbed the tree completely + rinne sharingan...shortly later he was killed by Zetsu. He hadn't even begun his proper full and direct attack on Naruto and Sasuke after attaining everything he could. Post mugen tsukuyomi activation, <i>(and with all minor pieces outta the picture, and attainment of his goal)</i> we didn’t even get to see his peak powers, that leaves a lot of scope for Madara
</p><p>Oh and for Naruto or anyone who doesn't possess a rinnegan <i>(don't know whether the tenseigan can dispel it)</i> with Mugen Tsukuyomi dispelling powers--- on a one to one fight to the death, Madara just has to send his limbos to deal with and distract them, and activate the Infinite Tsukuyomi + Nativity of god trees for a short time ...till the complete chakra of the opponent escalates quickly, leaving behind a white zetsu <i>(Unless they fight on a moonless dimension/planet)</i>
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Madara vs Toneri/Momoshiki: Toneri gets owned, haven’t seek Boruto the movie yet, so can't say about Momoshiki
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Madara vs. the rest individually: Madara dies of boredom/gets killed by Tenten's weapons
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</p><p>Kishimoto claimed that Madara had no weakness. After some time, Kishimoto himself defeated Madara the worst possible way with <i>plot no jutsu</i> o.O
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