This achievement is 1 of a few that is glitched in this game. I just finished beating Tony every round of the match...accumulating 960,000. During the game, i WON every round. I never 'pushed'. Here is a video clip of the last round where i went 'all in' with 640,000 and hit a black jack. No achievement popped. I also won every round against Mark using Kamiko and no achievement popped niether.