It felt quite similar to that each time, as Max believed that an opportunity had presented itself and he struck, but it turned out to be different from what he originally thought it to turn out like.
He might have hit his intended target in the past, but the results started to go in favour of Ash later as he missed her more often and was left trying to recover from his failure. "Damn..."
That experience only caused him to become more vigilant about taking on such risks, and he started to second-guess himself each time.
Even if he saw an opportunity, he was no longer so fully committed that he would be willing to throw enough power behind his attacks in a way that could let him do any real damage to her and let him win.
He tried to recover after missing as he followed up with a swing of his other arm toward where he thought Ash would be, and he tried to turn his body to face her as he did that.