The front game of Winning Streak is played in somewhat of a tournament fashion. In the first game, the champion faces off against a challenger. Both players are shown a grid of 16 letters, and a category which they must satisfy. (For example, "Parts of a book".) The challenger picks a letter, and host Cullen reads a clue to a word beginning with that letter. (Think Blockbusters.) Whoever buzzes in with the right answer gets to control that letter and has the choice of placing it on their board in one of seven slots or refusing it, then picking another letter off the board. The first player to complete a word with the letters they control wins the round and moves on to the next round.
In the second round, the contestant goes it alone against the big board. To start, the player chooses one of six numbers off the board; hidden behind that number is a cash value from $100 to $200. Then, the other 12 spaces on the board are put in play. The contestant chooses one of them and finds a letter. At that point, the contestant has 5 seconds say a word that contains that letter. If successful, the player gets that dollar amount and can then choose to keep it or go for double. To do that, the player chooses another space, finds another letter, and must give another word that contains the letters uncovered. This process continues until either the player calls it quits or stumbles.
A second game is then played with two new contestants. If the winner of either match craps out in the money round, then the other player is automatically crowned the champ. Otherwise, they face off in the final round.
End Game Rules
In the final round, the two winners from the front game face off in a one-on-one showdown. The top winner of the two gets the choice of going first or second. They then take turns picking spaces off the board, trying to come up with a word that contains all the letters shown. They continue until one player trips up, at which point the other player becomes the new champion and wins the combined total of their scores from the second round.