In the top of the second, Darren Lewis scored on an infield hit to give Boston a 3-0 lead, but the Yankees' resilience showed itself in the bottom of the inning.

Rod Beck came on in relief for the Red Sox and promptly gave up a leadoff homer to Bernie Williams win the game for the Yankees.

Thursday, October 14, 1999, at Yankee Stadium (I) in Bronx, New York Game 2 pitted Ramón Martínez against David Cone.

In the seventh inning, Ricky Ledee drew a leadoff walk, moved to second on a sacrifice bunt, and scored on Chuck Knoblauch's double to tie the game.

Saturday, October 16, 1999, at Fenway Park in Boston, Massachusetts Game 3 was the long anticipated matchup between Pedro Martínez and Roger Clemens, but the Red Sox would come out swinging, scoring in all but two innings.

Clemens was done in the third inning after allowing a leadoff single to Mike Stanley as Red Sox fans chanted "Where is Roger?"

Next inning, Yankees left fielder Ricky Ledee's error on Daubach's fly ball allowed Troy O'Leary to score all the way from first.

Sunday, October 17, 1999, at Fenway Park in Boston, Massachusetts Game 4 pitted Andy Pettitte against Bret Saberhagen.

The Red Sox would tie it in the bottom half when Butch Huskey doubled with one out and scored on Troy O'Leary's single.

In the fourth, Bernie Williams singled with one out, reaching second on an error, before scoring on Tino Martinez's double to tie the game.

After Darryl Strawberry was intentionally walked and Scott Brosius struck out, another error on Chad Curtis's ground ball allowed Martinez to score to put the Yankees up 3−2.

This game also featured the infamous trash throwing incident by fans when Jimy Williams was ejected from the game after arguing when Nomar Garciaparra was called out at first in the ninth inning, which followed a blown call by umpire Tim Tschida on Chuck Knoblauch's tag attempt on José Offerman in the eighth inning.

They added to their lead in the seventh when Jeter reached second on an error and moved to third on Paul O'Neill's single off of Derek Lowe.

Rhéal Cormier walked Bernie Williams to load the bases and another error on Chili Davis's ground ball allowed Jeter to score before Tino Martinez's RBI single made it 4−0 Yankees.

The only other team to match the 1999 Yankees one loss record in a single postseason in the Wild Card era was the 2005 Chicago White Sox, who also won 11 games and lost once.

After the season, Pedro Martinez was beaten out for the 1999 American League Most Valuable Player Award by Rangers’ catcher Ivan Rodriguez due to being left off the ballot of two voters completely by Minneapolis’ LaVelle Neal and New York’s George King.

In the previous season, King had put two starting pitchers on his MVP ballot, the Yankees’ David Wells and the Texas Rangers’ Rick Helling.

In the 2003 American League Championship Series, the Yankees beat the Red Sox on a game seven walk-off by Aaron Boone home run in the 11th inning.