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Gear 4 Luffy (Big Mom saga) vs Piccolo Jr (Dragon Ball Classic)

I'd give this to Luffy with medium difficulty via higher AP and durability while in his Gear Fourth forms, Precog via Kenbunshoku which would make it difficult for Piccolo to actually land attacks on him, homing attacks, better agility / maneuverability and even higher AP than usual with King Kong Gun and King Cobra.
 
Piccolo's physical strikes are not strong enough to bypass Luffy's elasticity (But only vs Gear 4th), his rapid fire attacks can be easily evaded due to Luffy's pre-cog and flexibility, so he'd have to resort to wide-ranged AoE attacks like what he did towards the end of his fight with Goku, but Luffy can tank this with little issue so Piccolo would be throwing his stamina out of the window to use attacks like this.

On the other hand, Luffy can only maintain Gear 4th for around 25 minutes under normal circumstances and he will be rendered unable to use Haki for 10 minutes when he exits the form. During this time, Piccolo could easily kill him.

However, that's assuming he can withstand fighting any of the Gear 4th modes for that time without being severely injured and fatigued, or flat out losing. He'd at least be the former, and possibly the latter in a 25 minute time-frame of them fighting, which I seriously doubt Piccolo could handle especially given that Luffy also has access to Tank-Man and Snake-Man, the former being useful for trapping opponent in his rubber torso, and the latter granting homing attacks that gradually increase in speed the more it stretches and turns. Bound Man has both of these powers to a more limited level.

There's also King Kong Gun and King Cobra which are vastly stronger than Luffy's normal attacks, so he'd probably one-shot if he needs to resort to one of them. Piccolo could evade KKG, but KC is a homing attack, so good luck with that.

Luffy's Advantages: AP, Durability, Pre-cog, homing attacks, gradual speed increase w/ Python (even tho speed is equalized, I heard that speed boosts still count here, correct me if i'm actually wrong), versatility, stamina, and resistance to blunt trauma

Piccolo's Advantages: Regenerationn (though limited), Higher base stats compared to Base Luffy (more than double, in fact--which may not factor), AoE.

Winner: Luffy mid-diff.

Also, I added more topics to the thread since you just had Luffy.
 
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