Andy Pettitte's Five Biggest Wins With the New York Yankees

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With 250 Wins, Andy Pettitte Deserves a Place in Cooperstown... Eventually

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Andy Pettitte decided it was time to don the Pinstripes once again.

Andy Pettitte returned to the mound for the New York Yankees on September 19 after being out since June 27 with a broken ankle. In true Pettitte form, the native Texan steered his way through five innings and was the winning pitcher in the Yankees' 4-2 victory over the Toronto Blue Jays.

Up until the injury, Pettitte was in a groove after his one-year (2011) retirement. It was the 244th triumph in a career that has spanned 17 seasons -- 14 in New York and three in Houston.

During that time, Pettitte has won a number of big games, but here's what I think are the five biggest:

5. September 4, 1996

Left-handed pitchers have always been a prized commodity for the New York Yankees, especially when they played at the old Yankee Stadium with its deep left field and even deeper power alley for right-handed hitters. The 24-year-old Andy Pettitte was in his second season in the major leagues when he established himself as one of top lefties in the game.

The 1996 season found the Yankees on their way to just their second postseason appearance since 1981, with Pettitte helping to lead the way. He took the mound on September 4 looking to become the first Yankees pitcher, and left-hander, to win 20 games since Ron Guidry reached the milestone in 1985.

The opposition was the Oakland A's, who had played sub-.500 baseball to that point in the season. The Yankees jumped all over A's starter Dave Telgheder for six runs through the first three innings. By the end of the fourth inning, the A's had cut the lead in half, but Pettitte settled down and blanked Oakland over the next three innings.

Pettitte's night was done, but he watched his teammates add four insurance runs in the eighth en route to a 10-3 win to earn Pettitte's 20th victory of the season. Pettitte added another triumph nine days later against Toronto and finished the season 21-8 with a 3.87 ERA.

4. October 17, 2001 - ALCS Game 1

The 2001 Seattle Mariners won an AL-record 116 games and won the AL West by 14 games. They lost the league championship series the prior year to the Yankees and were out for revenge but had the misfortune of facing Andy Pettitte in Game 1.

Pitching in the postseason for the seventh straight year, Pettitte was dominant. He retired the first 12 batters he faced before he allowed a pair of hits and a run in the fifth inning. He allowed just one more hit in his final three innings of work, and the Yankees won 4-2.

The series went just five games, with Pettitte picking up the victory in the finale.

3. October 25, 2009 - ALCS Game 6

The 2009 season saw the Yankees win their first World Series since 2000. To accomplish the feat, the Yankees had to go through the Los Angeles Angels of Anaheim in the American League Championship Series. The Angels had been a perennial thorn in the Yankees' side for a decade and had twice knocked them out of the playoffs.

The Angels had won Game 5 out in L.A. and were trying to force a seventh and decisive game to reach their first World Series since they won it all in 2002. The Yankees' lineup faced left-hander Joe Saunders, who had allowed just two runs and six hits in his seven-inning Game 2 start. Pettitte, meanwhile, had blown a 3-1 lead in Game 3, and the Angels went won in extra innings.

Pettitte allowed an RBI single to former Yankees OF Bobby Abreu in the third inning, but it was the only run he would allow in 6 1/3 innings. The Yankees knocked a wild Saunders out of the game in the fourth inning with a three-run inning and went on to a 5-2 win for their 40th AL pennant. Pettitte scattered seven hits over six innings, walked one, and struck out six for his 15th career postseason win.

2. September 29, 1995

In early August 1994, the Yankees appeared to be on the precipice of a return to the playoffs for the first time since 1981. Then the players went on strike and the season was canceled. When 1995 rolled around, the Yankees knew they had an excellent chance to make the postseason, especially since a wild-card playoff participant had been added to each league.

The Yankees couldn't catch Boston for the AL East division lead, but were in a tight battle with the Seattle Mariners and California Angels (who were also in a battle for the AL West title) for the new playoff spot. Pettitte was the scheduled starter when the Yankees and Toronto Blue Jays met in the first game of a season-ending three-game series.

Pettitte limited the Blue Jays to just four hits over eight innings, but the Yankees trailed 3-0. Pettitte had been outpitched by Juan Guzman but he kept his team in the game, and the Yankees responded in kind by scoring four runs in the top of the ninth against reliever Tony Castillo.

Second baseman Pat Kelly hit a line-drive home run, just his fourth of the season, to left field to put the Yankees on top for the first time all day. The victory clinched the wild-card spot for the Yankees and gave Pettitte his 12th win of the season. Pettitte's 12-9 record helped him to finish third in the AL Rookie of the Year vote.

1. October 24, 1996 - World Series Game 5

Pettitte had been humiliated in Game 1 of the World Series against the Atlanta Braves. It was the Yankees' first World Series appearance since 1981, and it was a most forgettable beginning.

Pettitte was hammered for seven runs in just 2 1/3 innings, and the Yankees lost 12-1. After a scoreless first inning, the left-hander allowed a pair of runs in the second inning and five of the six runs Atlanta scored in the third inning. Included was a home run to Pettitte's current teammate with the Yankees, Andruw Jones.

The Yankees lost Game 2 as well and headed to Atlanta in 2-0 hole, but won the first two games in Georgia to even the series. Game 5 was a rematch between the opener's victor, John Smoltz, and Pettitte, who faced a mountain of pressure to put the Yankees in position to win the series when they returned to New York for Game 6.

But the Braves met a different Pettitte the second time around; the lefty struck out three of the four batters he faced and cruised through eight innings with a 1-0 lead. Chipper Jones led off the ninth inning with a double, just the fifth Braves hit of the day. Pettitte retired Fred McGriff and then watched as John Wetteland saved his victory.

The Yankees went home up three games to two and won the World Series in six games.

Drew Sarver has been a Yankees fan for over 40 years and has blogged about them on his site My Pinstripes since 2005. You can follow him on twitter at @Mypinstripes.

1 - Statistics and Game Details courtesy of

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