1996 World Series: In the defining game of his career, at age 24, outduels that year’s N.L. Cy Young winner, John Smoltz, in Game 5 of the deadlocked World Series, throwing 8 1/3 innings shutout innings in Atlanta in the Yankees’ 1-0 win.
AP
2 of 11
1997 ALDS: Pettitte goes 0-2 with an 8.49 ERA against the Indians, which includes a loss in the deciding fifth game in Cleveland.
AP
3 of 11
1998 ALCS: The 114-win Yankees fall into an unthinkable 2-1 hole in the series after he allows six runs on four home runs in 4 2/3 innings.
AP
4 of 11
2001: Pettitte earns the ALCS MVP after winning the first and final game of the series against the 116-win Seattle Mariners.
AP
5 of 11
2001 World Series: One win away from the Yankees’ fourth straight title, and fifth in six years, Pettitte loses his second game of the series after getting shelled for six runs in only two innings of a 15-2 loss at Arizona.
AP
6 of 11
2003 World Series: Pitches well again after nearly throwing a complete game shutout in his Game 2 win, but can’t match Josh Beckett’s brilliance, and is the losing pitcher in the Marlins’ title-clinching game at Yankee Stadium.
Jeff Zelevansky
7 of 11
After being named in the Mitchell Report in 2007, Andy Pettitte he used HGH.
Reuters
8 of 11
Sept. 19, 2007: Pettitte wins his 200th game in a victory over the Orioles
AP
9 of 11
Sept. 21, 2008: The Core Four pose together after Pettitte makes the final start at the old Yankee Stadium and records his 2,000th strikeout.
Getty Images
10 of 11
2009 : Wins the clinching game of three postseason series’, including the Yankees’ Game 6 win over the Phillies in the World Series on three days rest. It was the team’s first title since 2000.
Charles Wenzelberg
11 of 11
June 8, 2013: Pettitte registers his 250th win in a victory over the Mariners in June, becoming only the 47th pitcher to reach that milestone.