If you're having a difficult time beating the pros in the game in a game of SKATE, try the following. Since the pro always goes first when you challenge them, keep resetting your game until the pro messes up his first trick.

At this point, you can break out some difficult tricks that will allow you to beat the pros each and everytime. Do a 540 spin in variations (Ollie 540s, Nollie 540s, Kickflips, Heelflips, et cetera). Doing this will defeat your opponents easily because they won't even attempt to repeat the hard trick you just did. Easy victory!