In the 2003 ALCS, Wakefield allowed four runs over 14 innings against the New York Yankees. He started Games 1 and 4 of the Series against Mike Mussina and won both starts. He was also called in to pitch in extra innings of Game 7, after the Yankees tied the game. The Red Sox had been leading 5–2 in the eighth inning. After retiring the side in order in the 10th, Wakefield gave up a home run to Aaron Boone on his first pitch of the 11th, sending the Yankees to the World Series. Wakefield apologized to fans after the game.