In the anime they haven't yet. But my prediction is that if they fight eventually Luffy will own him. Mainly because he can hit logia users with haki now.
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153 to bout 190's
The fight between Luffy and Crocodile starts from episode 122
Their first fight is over episodes 435 and 436, their second fight is 449 and 450.
I'm presuming your refering to the fight between Luffy and Usopp back on Franky's island WaterSeven/Aqua Lagoona. Well they were fighting over whether they should leave their ship, Merry, behind as it had become broken beyond repair after their visit to the Sky Island. Usopp wants to save and repair the Merry, but Luffy see's sense and knows it's safer to leave the Merry behind. Usopp challenges Luffy to a dwell, which Zoro forsees and prevents the others from getting involved and stopping them. Luffy, enevitably, wins.
yes but he has to absorb about 100 shadows to become nightmare Luffy