We were at WDW for an extended vacation last year staying at the Boardwalk, and I was thinking about spending an afternoon at ESPN to watch the games, drink, etc.
I wandered down to the Bakery (which is very close to ESPN) for breakfast one morning and there was already a line to get in - I think it was about 10am. At that point, I started to make alternate plans.
I think showing up towards the end of the second games is a good idea. But if it's packed, Big River, which is also on the Boardwalk, will have the game on. Their food as a whole isn't great, but the appetizers are good and the burgers are among the best in WDW. Oh, and the beer is pretty good too!