The 5 Kage attack Kabuto in his cave
Kabuto should win, mainly due to the Kage's lack of defensive techniques.
Gaara might be able to grind, but his sand quantity won't be nearly as much as before. Without Susano'o, I see Kabuto picking them off with techniques like Muki Tensei and Bone Forest. He can take them all out with Tayuya's sound Genjutsu simultaneously, and they lack the Sharingan to be able to break each other out of it.
Despite the numbers advantage, the Kage will lose here.
Sasuke and Edo Itachi fight Obito
The Bijuu will get trolled by Amaterasu if they resort to full form, so it depends whether they opt for BM or V1 / V2. I personally think V1 / V2 is more beneficial as they don't make themselves huge targets and can also utilize their special Bijuu abilities.
Regardless, their inability to hit Obito will be their demise here. Obito was handling a far more powerful team and they only managed to put the pressure on him due to Kakashi's presence.
Naruto, bee, gai, and kakashi take on edo Masada
Madara gets destroyed here.
Tired Gai knocked Madara's V3 Susano'o on his ass and continuous Bijuudamas will tear anything that isn't Perfect Susano'o apart. Hachibi and Kyuubi's combined Bijuudama will probably be enough to blow up Perfect Susano'o considering they intended it to destroy Gedo Mazo moments before it became the 10 tails. Madara's lax fighting style also means he is a prime candidate for getting Kamui warped.