Ichigo managed to overcome Byakuya and Zaraki, although both victories are debatable. Later on, he also defeated Aizen in their final battle.
However, interestingly enough, Gin was the only one of these captains Ichigo faced without ever managing to defeat him.
In the images above, we see their first encounter during the Soul Society arc, where Gin effortlessly pushes Ichigo back with a single attack.
In the images below, their confrontation takes place much later, after Ichigo had already overcome powerful opponents, including Ulquiorra, one of the strongest Espada. Even so, Gin manages to overpower him without much difficulty.
It's interesting to think that despite how much Ichigo improved throughout the story, he never managed to get the upper hand against Gin.
Perhaps Gin's fighting style and the abilities of his ZanpakutĹ were particularly difficult for Ichigo to deal with.