He never had a chance to win. For if he let her drink 3 cups, it would be a testament to how little he cares about her and damage their already fractured relationship even more.
@Nep What he tried to do to win was to lose one or two time to drink at least one poisoned cup so that Maomao would only have two poisoned one at most and then win in the end. That way he could have won knowing he wouldn't poison her. But that was without counting on eve cunning Maomao of course.
Am I the only one seeing this panel or something? That means he meant to lose from the start, probably at the point when Mao Mao told him to buy the courtesan. But everyone seemed to be talking about how Mao Mao owned him.
MaoMao >>>> any female protagonist "divine doctor" bs because she actually uses real medicine instead of "traditional" medicine (cough cough pseudo-medicine cough cough)