Well, it's his way of portraying Kaido. Who isn't really going into 1 on 1s to prove his superiority, he is more of the guy to attack groups of people who are superior, hence getting defeated and captured many times but with people recognizing Kaido's strength and inability to get killed. Hence Oda, in the same chapter of saying "In a 1 on 1, always bet on Kaido", also saying that he lost multiple times in the past.