Luffy might win ... which is quite odd to me.
Luffy gets defeated twice by Moriah comes back takes the "W"
Luffy loses twice against Crocodile comes back takes the "W"
Luffy gets massacred by Kata comes back takes the "W"
This formula Oda has been using might come into play again, Luffy gets slapped around only to come back with a new technique or learning from his opponents, matches them and wins.
At the same time though Kaido is heavily wounded so Kaido would technically still hold onto his "1v1 always bet on Kaido title"
Luffy gets defeated twice by Moriah comes back takes the "W"
Luffy loses twice against Crocodile comes back takes the "W"
Luffy gets massacred by Kata comes back takes the "W"
This formula Oda has been using might come into play again, Luffy gets slapped around only to come back with a new technique or learning from his opponents, matches them and wins.
At the same time though Kaido is heavily wounded so Kaido would technically still hold onto his "1v1 always bet on Kaido title"