Why doesn't pip enjoy the victory over the pale gentlemen?

Answer 1

Pip worries about his victory over the pale gentleman because he knows that he should not have picked a fight with a gentleman. He believes that the law will eventually punish him for being so disrespectful. The pale gentleman, named Herbert Pocket, later becomes friends with Pip once Pip comes into money.

Answer 2

Pip doesn't enjoy the victory over the pale gentlemen because he realizes that the wealth and success he gained came at the expense of maintaining loyalty to his benefactor, Joe. He recognizes the shallowness and moral cost of his actions, hence the lack of true satisfaction in his accomplishment.