Double S.T.E.A.L: The Second Clash has the same reckless vehicular smashing action of the first game, but this time set in the American city of Chicago. Missions can have varied objectives such as destroying a number of Yakuza targets or getting to a point in the city while being hounded by Yakuza cars. Missions have far more generous time limits compared to the first game, but they are also now rated, and earning a high rating on a mission with a quick time can unlock Extra Missions and cars. Most cars can earn multiple turbo boosts by destroying property and traffic, and if the boost bar is maxed out then it will be expelled all at once and stop time as well.

The free mode of the PlayStation 2 and GameCube versions of Wreckless makes a return, allowing Madoka and Mei to drive around the city without worrying about objectives or time limits. Boxes of car parts can be found hidden around Chicago, and for every five boxes found a new car will be unlocked. Extra Missions can be found as well that have non-Yakuza related objectives, such as winning a dirt race, reaching checkpoints, or delivering pizza in time.

Having already freed Hong Kong from the grip of the Yakuza in their last game, the Dragons of the Hong Kong Police Force fly to America to hand Tiger Takagi off to the CIA. Unfortunately Takagi is barely on American soil for five minutes before his Yakuza cronies spring him, and this time it's up to the Dragons alone to put him behind bars for good.