The best Yankees postseason moments since 1999

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New York Yankees’ Todd Frazier reacts after hitting an RBI triple to left field abasing the Cleveland Indians during the second inning in Game 4 of baseball’s American League Division Series, Monday, Oct. 9, 2017, in New York. (AP Photo/Frank Franklin II)

Welp, this stinks.

It’s going to be a long offseason since the Yankees had a problem with the Houston Astros in what was a heartbreaking ALCS for bombers fans. 

Though, we here at  amNewYork want to look on the brighter side and acknowledge that despite this recent disappointment, there’s been plenty of October magic in the past 20 years from 1999-2019. 

These are in no particular order and  you get to fill out your own scoresheet on how to rank ‘em. 

The only criteria on the list is that the Yankees had won the series in which said moment(s) occurred:

World Series Titles: 


The most recent title that the Bombers proudly claim came against Philadelphia ten years ago. After taking a first game loss, this six game series saw the Yankees pull out three in a row from Philly and later locking down number 27 in a no contest final game the Bronx. 


Be sure to put this in the face of any spiteful Mets fan that’s had too much of a mean spirited laugh in the past 30 hours. This series started off with a 12th inning walk-off win for the Yankees in the Bronx followed by an overall domination of the Mets resulting in the five game crush for World Series number 26. 


The only thing better than winning the World Series is stomping all over the Boston Red Sox in five games beforehand. David Cone also threw is perfect game in that 1999 season before the Yankees would go on to sweep the Atlanta Braves to collect the franchise’s 25th overall and third straight year of jewelry. 

Memorable moments: 

2011 ALDS Game 3: “The Raul Ibanez Game”

“Did he do it again?” Trailing 2-1 against the Baltimore Orioles in bottom the 9th, short tenured Yankee Raul Ibanez steps in the batter’s box and creams a ball into the right field seats, evening the score at two apiece. He gets back up in the 12th inning and flys another one into the right field upper deck, giving the Bombers a 3-2 win and 2-1 series advantage. 

2003 ALCS: “Boone A Hero in Game 7”

We’ve all dreamed about blasting a walk-off homer against the Red Sox in extra innings to lift the Yankees into the Fall Classic, but the current Yankees skipper lived it during the 2003 ALCS. 

2017 ALDS: Cleveland Comeback

After taking two against the Indians, a scrappy Yankees squad would find the resiliency to win three in a row bolstered by a pair of homers from Didi Gregorious in the decisive game 5. 

1999 ALCS Game 1: Bernie’s Walk-off

Number 51 comes to the plate in the 10th inning of game one against the Red Sox and shoots one over the wall in straightaway centerfield, ‘nuff said. 

2009 ALDS Game 2: Twin Homers Against Minnesota

Trailing 3-1 in the bottom of the 9th, A Rod puts a 2-run shot into the Yankee bullpen before Mark Teixeria clocks a walk-off into the left field seats in the 11th.  

2017 Wild Card: A Gregorian Blast

Trailing 3-0 in the bottom of the first, Sir Didi Gregorious comes to the plate and ties the one game playoff with a blast to the short porch, putting much needed life back into the Bronx. The Yanks would go on to complete the 8-4 comeback after onslaught of offense firing from all cylinders. 

Just remember:

The reality is that the Yankees are going to win it all in the next five years. Not even Sox, Mets, nor Astros fans can deny the inevitable truth to this.