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The 25 Best Yankees Games of the Past 25 Years

A salute to the best regular season showdowns in recent memory.

Dan Brink

Something I love about baseball — and something that I’m glad we will indeed get to see again in 2022 — is that you never know what’s going to happen on a given day. The odds might be completely stacked in one direction. After all, why on earth would anyone expect Don Larsen to throw a perfect game in the World Series against the defending champions after getting clobbered by them just a few days prior?

But that’s the magic about this goofy sport. A game can end in utter chaos thanks to a fan running onto the field during the planned last pitch. A second baseman with just 23 career homers in 421 games can hit the decisive blast to send a beloved captain to the postseason for the first time — and that’s to say nothing of the light-hitting shortstop who earned himself a nickname with a memorable shot of his own to down the Red Sox in Game 163.

These were all regular season matchups, and ones fondly remembered by both the fans who watched them and the younger generations who heard the stories. The past 25 years have witnessed their own share of Yankees classics too, and over the next month, the Pinstripe Alley staff is going to take turns remembering the best of the best. At some point in the future, we may revisit the best playoff games, but these showdowns in the heart of the season itself have stuck in fans’ memories for a very good reason.

Jake will kick us off today by remembering a perfect day for David Wells in 1998, and we’ll continue this series every weekday until mid-April. Enjoy!

5/17/1998 - David Wells’ perfecto
5/19/1998 - Armando Benitez fight night
7/18/1999 - David Cone’s perfecto
6/19/2000 - The 22-1 demolition at Fenway
9/2/2001 - Mike Mussina’s near-perfecto
5/17/2002 - Jason Giambi’s rainy walk-off slam
7/1/2004 - The Derek Jeter dive game
4/26/2005 - Alex Rodriguez’s 10-RBI night
6/21/2005 - 13-run 8th completes 8-run comeback
5/16/2006 - Jorge Posada leads huge comeback
8/20/2006 - Jason Giambi provides apex to 2nd Boston Massacre
4/19/2007 - A-Rod’s walk-off bomb caps ridiculous comeback
6/7/2008 - Johnny Damon’s six-hit, walk-off day
5/15/2009 - Melky Cabrera kicks off Walk-off Weekend
6/12/2009 - The Luis Castillo Game
7/9/2011 - DJ3K Day
8/25/2011 - The Three-Slam Game
4/21/2012 - 9-0 comeback in Boston
9/22/2012 - Ibañez previews playoff heroics
9/25/2014 - The Captain’s walk-off farewell
4/28/2017 - Matt Holliday walk-off caps eight-run comeback
6/29/2019 - Slugfest in London
7/23/2019 - Mayhem marathon in Minnesota
5/19/2021 - Corey Kluber’s no-hitter
7/10/2021 - Gerrit Cole’s masterpiece in Houston