You don’t have to be an enemy to fight someone

Don’t matter, wasnt a fight. Fight is both committed to fight, garp js beat him on the head. Ace never fought him.

Neither did boa,

Okay but when Luffy was a child wanting to fight Garp and Garp wanted to shut him up surely that counts

Doesn’t

Does…

Does…..n’t

Doeszzzzzz!

Idk. Ace bc they had practice fights, but Chinjao bc he was the first conquerors user Luffy actually fought against. He never actually fought against Hancock, and idk if I can count Garp since most of the time it was either play fighting or Garp letting Luffy hit him (Marineford).

I'ma go with Chinjao bc he was the first serious character Luffy actually faced off against with conquerors haki.