Proving Ground features gameplay that is more reminiscent of earlier Tony Hawk games, whilst including new features such as Nail-The-Manual and Nail-The-Grab. These are similar to the Nail-The-Trick mode from the previous game, Tony Hawk's Project 8.
There are 9 levels in the game. They are in 3 East Coast cities, Baltimore, Philadelphia, and Washington, D.C. The levels differ between the different console versions. In the Xbox 360 and PlayStation 3 versions, there is one open world. In the Wii and PlayStation 2 versions, levels have to be selected by pausing the game. Three different types of goals in Story Mode are available; Rigger, Career, and Hardcore. In each level, there are two arcade machines, one for high scores and the other to play classic mode. This game has three Nail the Trick modes (Nail the Trick, Nail the Grab, and Nail the Manual). The PlayStation 2 and Wii versions do not include the Nail the Manual feature. The Classic Mode feature allows the player to play each city section in the style of early Pro Skater games. There is a Free Skate mode on the PlayStation 3, Nintendo DS, and Wii versions.
The game is the first installment in the Tony Hawk's series which allows online features via the PlayStation Network. One can host or join an online party, which allows up to 4 players, who are able to free-roam in one of the three cities. The players can also invite other players to their Skate Lounge, a fully-customisable warehouse in Philadelphia, where one can put ramps, rails, items, and even challenges.