Yankees: 5 Best Playoff Games of the ’90s Dynasty

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The New York Yankees won four World Series in five years, and finished plenty of classic playoff games along the way.

You don’t become a four-time champion in five seasons without winning a couple of playoff classics, and Yankees fans are well aware that just because you win more often than not doesn’t mean you didn’t sweat through the entire process.

Though New York won 10 playoff games per season in 1996, and 1998-2000 (and piled on another nine in 2001), the road to get there was long and arduous.

These playoff games took years off Yankees fans’ lives, but in retrospect? They were total classics.

Oh, and we’re sticking ’96, ’98, ’99, and ’00 here. Sorry, Derek Jeter’s Flip Game — the Yankees couldn’t finish the job that year.

Yankees

NEW YORK, UNITED STATES: Baltimore Orioles’ Brady Anderson hits a solo home run off the New York Yankees pitcher Andy Pettitte in the second inning of the American League Championship Series at Yankee Stadium 09 October. AFP PHOTO Henny Ray ABRAMS (Photo credit should read HENNY RAY ABRAMS/AFP via Getty Images)

5. Game 1, 1996 ALDS

The Yankees battled the Orioles in a game eventually defined by a random teenager.

This game is downgraded by me, personally, because it’s the only one the haters are correct on. Yes, it’s kind of a chintzy Yankees victory. No, they don’t tie the game without the help of Jeffrey Maier. That’s just accurate.

But, that being said, it began a dynasty, and started a five-year chunk of the NYY earning the breaks. Also, it was a hell of an iconic game.

Down 4-2 in the bottom of the seventh inning, a Darryl Strawberry bases-loaded walk drew New York one run closer. In the eighth, rookie Derek Jeter lifted a long, fly ball into right field that found leather…which belonged to a fan, leaning well over his allotted boundary.

What’s often forgotten: Mariano Rivera navigated through two tough innings, shutting Baltimore down in the 10th and 11th, despite putting two men on with two out for Mike Devereaux in his first inning of work.

Bernie Williams walked things off with a leadoff dinger against Randy Myers in the 11th, and New York went to Joe Torre’s first World Series as manager four games later, finishing the series off at Camden Yards.

It goes without saying, but after the Yankees held home court here, nothing was the same. They actually lost Game 2 (!) before winning three consecutive road games. Heart of a champion.

Take away credit for Maier, but give it right back for that resolve.

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