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The 25 Best Yankees Playoff Games of the Past 25 Years

We’ve been lucky enough to see a plethora of great Yankees postseason games since the ‘90s. Join us as we remember the best of the best.

Dan Brink

Earlier this year as the MLB lockout came to a close and teams began to assemble for the beginning of the 2022 season, the Pinstripe Alley staff collaborated on a rundown of the best Yankees games of the past 25 years. It was a lot of fun to revisit those games, and there were some absolute classics that stand the test of time.

And yet, for as thrilling as it was to see David Cone achieve perfection, Derek Jeter reach 3,000, and for Aaron Hicks to cap a truly outlandish marathon in Minnesota, none of these moments really compare to the chaos of the MLB postseason. It’s one thing for Raúl Ibañez to pinch-hit and homer twice off the bench in 14 innings against the A’s in late 2012; it’s another to do what he did* a couple weeks later in the Division Series with the Yankees inching ever-so-close to elimination.

*Yeah, yeah, #spoilers, but whatever. If you’re older than 10, then you knew that it would be on the list anyway.

So with plenty of time remaining until pitchers and catchers report, we’re kicking off a review of the best 25 Yankees playoff games of the past 25 years. It’s the logical next step from our previous offseason series project, and one that’s going to be a blast to read.

The series begins this morning with Matt discussing a World Series opener — starring one Constantino Martinez — that those who watched will never forget. The series will run on weekdays in chronological order until mid-January, when we’ll reach the most recent addition to the list (this article will update with new links every day). We look forward to this walk down memory lane together!

1998 World Series Game 1 - Tino slams the Padres
1998 World Series Game 3 - Brosius’ MVP-making night
1999 ALCS Game 1 - Bernie walks off Boston
2000 ALCS Game 4 - Rocket lifts off in Seattle
2000 World Series Game 1 - Vizcaíno’s Subway Series walk-off
2000 World Series Game 5 - Sojo’s thousand-hopper wins Subway Series
2001 ALDS Game 3 - The Flip
2001 ALCS Game 4 - Soriano shocks 116-win Seattle
2001 World Series Game 4 - Tino & Mr. November win it
2001 World Series Game 5 - Brosius and November magic
2003 ALCS Game 3 - Brawling in Boston
2003 ALCS Game 7 - Aaron F-in’ Boone
2009 ALDS Game 2 - A-Rod steps up vs. Joe Nathan
2009 ALCS Game 2 - A-Rod to the rescue again
2009 World Series Game 2 - A.J. Burnett’s career night
2009 World Series Game 4 - Damon, A-Rod steal one in Philly
2009 World Series Game 6 - “The Yankees are back on top”
2010 ALCS Game 1 - Big comeback in Arlington
2012 ALDS Game 3 - Raúl, so cool
2012 ALDS Game 5 - CC sends Yanks to ALCS
2017 AL Wild Card Game - Bullpen, bombs pick up Sevy
2017 ALDS Game 3 - A Tanaka gem and a Bird bomb
2017 ALDS Game 5 - Didi caps ALDS comeback
2017 ALCS Game 4 - Judge keys rally over Astros
2020 ALWC Game 2 - Gio slams Yanks past Cleveland

Best of the Rest
2000 ALCS Game 6 - “Get your tokens ready”
2004 ALDS Game 4 - A-Rod, Sierra stun Twins
2019 ALDS Game 2 - Didi slams Minnesota
2019 ALCS Game 5 - Hicks, Paxton save season
2022 ALDS Game 4 - Cole steps up