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

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.

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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4. Game 4, 1998 ALCS

The Yankees really needed El Duque to step up in ’98. He did.

The greatest team in Yankees history temporarily forgot to win games in the middle of the 1998 postseason.

Still reeling from the Chuck Knoblauch extra-innings boner in Game 2 of the ALCS, the NYY dropped Game 3 in Cleveland, too, 6-1. Did New York overestimate their own mental fortitude?

Nope. Orlando Hernandez toed the rubber on the road in Game 4, and put a Pedro Martinez-like stop to Cleveland’s momentum. From the very first pitch, he had The Land mesmerized.

Hernandez threw seven three-hit innings, walking two, whiffing six, and throwing 115 pristine pitches. Oh, and it was his POSTSEASON DEBUT. No big deal.

This start gets the nod because of its importance in the big picture. Without Hernandez’s herculean effort, there’s a good chance New York’s greatest single-season team would’ve fallen down 3-1 in a blink, squandering 114 regular season wins, thanks in part to one of the most embarrassing blunders in franchise history (Knoblauch yelling while a live ball rolled).

Instead, the ’98 Yankees got their well-earned Museum Collection status, and Hernandez became one of the great clutch pitchers of his era. Monumental swing.

3. Game 1, 1999 ALCS

The Yankees put the Red Sox in their place for the first time in the modern era in Game 1 of the ’99 ALCS.

Entering the 1999 ALCS, the Yankees hadn’t dispatched of the Red Sox in October since 1978, and Boston entered this battle very much believing in themselves.

After all, they had Pedro Martinez at his absolute peak. Who wouldn’t be confident?

Luckily for the Yankees, it took every ounce of Pedro to get Boston out of a five-game ALDS battle with the Indians; his no-hit relief appearance was the difference in that hard-fought series.

Martinez going all-out demoted him to Game 3 of the ALCS, and left Kent Mercker in line to start Game 1 at Yankee Stadium. Oops! Still, somehow, Orlando Hernandez spotted him a three-run lead, with a wild error resulting in two first-inning runs for the Sox.

Rather than fold, New York leveraged their reputation, and stormed back late.

Scott Brosius smacked a two-run shot off Mercker in the second, and Derek Jeter evened things with an RBI single against Derek Lowe in the seventh. The NYY held serve until their first batter of extra innings, Bernie Williams, greeted Rod Beck accordingly.

The series was over right then and there. New York let Pedro do his thing in Game 3, a blowout loss, but won the series in 5. Chess match. Checkmate, Yankees.

2. Game 4, 2000 ALCS

Yankees ace Roger Clemens lived up to his billing on the road at Seattle.

Roger Clemens joined the Yankees, amid much fanfare, after the 1998 season.

But that first year, many fans still preferred the jettisoned David Wells, and it was a fair assessment — Clemens posted a 4.60 ERA in 1999, just slightly above league average (102 ERA+).

Luckily, his 2000 season was a different story. Coming off a 13-8 record and 3.70 mark, Clemens finished sixth in the Cy Young race, and entered October with renewed ferocity.

It…didn’t go great. He took both Ls in a five-game ALDS victory over Oakland, sporting an 8.18 ERA. So when the Rocket toed the rubber in Seattle for Game 4 of the ALCS, he had a lot of doubters to prove wrong, and he set them all down looking. Clemens struck out 15 in a one-hitter, hurling an instant postseason classic.

The Yankees won this game 5-0, taking the first two in Seattle by a combined score of 13-2, ultimately taking a 3-1 series lead.

And yes, he threw eight two-hit innings against the Mets in the World Series, and also threw a shattered bat at Mike Piazza. The Clem-aissance started in front of a Tully’s Coffee sign at Safeco, though, in an instantly rewatchable playoff masterpiece.

We’re not done with this series, either.