Battles

VS

Round one Madara has EMS and Nagato and Itachi are not at full heath.

Round Two Madara has the Kyuubi and Nagato and Itachi are at full heath.

In Character

No Prep Time

Setting Valley of the end.

Round 1. Akatsuki wins with little Difficulty BUT if you Include Obito in the Akatsuki, they win with almost no difficulty...

Round 2. I'm gonna say The Akatsuki with HIGH difficulty, A FULLY healthy Nagato may be able to Seal/Compress the Kyubbui he almost did it in his fight against Naruto... Also A Totsuka Blade piercing the Nine Tails may seal it as well...

Everyone besides, Itachi, Nagato, and Obito are just their to hold down the 9 tails or fend off Madara...

@5th: Yes Madara's Susanoo > Itachi's BUT Itachi's susanoo has the better weaponry thanks to the sacred items it holds, The Yata Mirror and Totsuka Blade, I strongly believe if Itachi were to even PIERCE the Kyubbi it would be sealed...

Also take into account fighting A FULLY HEALTHY Nagato would mean your fighting him with all his powers, PLUS whoever he decides to use as a path, hell maybe he decides to use The Jhinchurki as paths just like obito did... Then the fight goes from being 2v10 to 2v16

In no way shape or form am I saying this will be EASY but I believe the Akatsuki with their combine efforts ESPECIALLY Itachi + Nagato + Paths can skid by a victory...