Years as Manager: 2002–2003
Regular Season Record: 188-136
Postseason Record: 6-6
Memorable Moments for Grady Little
- 11 March 2002 - Less than a month before the season is set to begin, the Red Sox replace interim coach Mike Cubbage with Grady Little.
- 16 October 2003 - New York takes Game Seven and the American League pennant with a 6-5, 11-inning win over Boston at Yankee Stadium. Up 5-2 with one out in the eighth, manager Grady Little leaves what appears to be an exhausted Pedro Martinez on the mound despite the bullpen having given up just two runs in the series. The Yankees score three runs on four straight hits to tie the score and win in the bottom of the 11th when Aaron Boone hits the first pitch he sees from Tim Wakefield into the left field bleachers to send New York to the World Series.
- 27 October 2003 - The Red Sox fire manager Grady Little despite having gone 188-136 in two years with Boston, winning 93 games or more in both seasons.