Complex sentence: The first two times Grocery Game was played, the contestant was given $100 at the start of the game; if they won the game or exhausted all five grocery items (but did not exceed $7.00), they kept the $100.
Split into simpler sentences: The first two times Grocery Game was played, the contestant was given $100 at the start of the game. If they won the game or exhausted all five grocery items (but did not exceed $7.00), they kept the $100.