Gai wins with the only problem being regeneration.
- He is faster than Juubito and Juubi Madara seeing how he kept covering the distance between Him
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(Middle right panel) and Madara easily
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and even surprisingly kept up with a Juubi Jin in a weaker gate . He'll be smacking Juubito around if it comes down to a CQC which would definitely be the case since Gai was below while Madara was in air. This guy ran circles while in mid air to the extent where the smoky substance around them were greatly affected
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and even Madara commented on his speed in the next page
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- Juubito's only chance is defending himself which isn't the case here since Gai has shown a direct EE can break through the Gudo dama.
- Now that he can touch the Gudo dama, any TSB thrown at him can be sent back to Juubito.
- Now that full intel is given, regeneration which is the biggest factor here can be dealt with. Gai can immobilize him with EE just like he did to Madara who's a superior version
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and given the fact that he strikes much faster, he can prepare NM right after while Obito can't move and then attack him with it and since Juubito would be immobilized, his only choice is to defend himself with the Gudo dama if anything since he isn't dodging such immense speed that distorts space while just recovering from the previous attacks and just being able to move if he eventually shakes it off.
Madara was almost killed from this, so Juubito can also be killed. If he survives then Gai loses.