In his second season with the Red Sox, Little guided the team to a record of 95–66 and an appearance in the 2003 American League Championship Series against the New York Yankees. Despite his accomplishments, Little is best remembered for his decision to leave starting pitcher Pedro Martínez in the eighth inning of Game 7 while the Red Sox held a three-run lead, and faced blame for the team's subsequent loss when the Yankees were able to tie the score and win in extra innings.