The 1999 American League Championship Series (ALCS) was a matchup between the East Division Champion New York Yankees (98–64) and the Wild Card Boston Red Sox (94–68). The Yankees had advanced to the Series after sweeping the West Division Champion Texas Rangers in the AL Division Series for the second consecutive year, and the Red Sox advanced by beating the Central Division Champion Cleveland Indians three games to two. The Yankees won the series four games to one and went on to win the World Series.
Both teams came into the series on a roll; New York had swept the Texas Rangers for the second straight year in the 1999 American League Division Series and Boston had come from two games down to defeat the Cleveland Indians in their division series. However, the Yankees won in five games. They would register their only postseason loss of the 1999 season in this series.
New York won the series, 4–1.
Wednesday, October 13, 1999, at Yankee Stadium (I) in Bronx, New York
Game 1 was a matchup between Kent Mercker and Orlando Hernández. The soon-to-be-named 1999 ALCS MVP got into trouble in the first two innings. After a leadoff single by José Offerman, John Valentin would reach on an error by Derek Jeter, scoring Offerman for the first run of the game in the first. Valentin would score on Brian Daubach's single to right. It looked like the Red Sox were ready to clobber the Yankees, but no more runs would score in the inning. Darren Lewis would score on an infield hit in the second to make it 3–0 Red Sox, but the Yankees' resilience showed itself in the bottom half. With Shane Spencer on first with two out, Scott Brosius slugged a home run to make it a one-run game. The duel continued into the seventh. With Derek Lowe now pitching, Brosius singled to lead off the inning. A sacrifice bunt by Chuck Knoblauch moved him into scoring position. Jeter would single to center and drive in Brosius to tie the game. Small ball helped the Yankees tie the game, but the long ball would win it in the bottom of the tenth. Rod Beck came on in relief and promptly gave up a leadoff homer to Bernie Williams to lose the game for the Red Sox. The Yankees had a one-game lead in the series.
Thursday, October 14, 1999, at Yankee Stadium (I) in Bronx, New York
Game 2 pitted Ramón Martínez against David Cone. After grabbing a 1–0 lead behind a solo home run in the fourth by Tino Martinez, the Red Sox responded in the fifth when Jose Offerman hit a leadoff single and two outs later, Nomar Garciaparra homered to put them up 2−1. In the seventh, Ricky Ledee drew a leadoff walk, moved to second on a sacrifice bunt, and scored on Chuck Knoblauch's double to tie the game. Tom Gordon relieved Martinez and walked Derek Jeter, then Rheal Cormier relieved Gordon and allowed a single to Paul O'Neill put the Yankees ahead 3−2. The lead would stand and Mariano Rivera, who won Game 1, got the save in the ninth to put the Yankees up two games going to Fenway Park.
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. After a leadoff triple by Jose Offerman in the first, John Valentin homered to put the Red Sox ahead 2–0. Next inning, Clemens allowed a one-out double to Trot Nixon and subsequent single to Offerman before Valentin's groundout scored Nixon. After Jason Varitek walked, Nomar Garciaparra's double scored Offerman to make it 4−0 Red Sox. Clemens was done in the third inning after allowing a leadoff single to Mike Stanley as Red Sox fans chanted "Where is Roger?" and then a response chant of "In the Shower". Hideki Irabu fared worse in relief as Brian Daubach's home run made it 6−0 Boston. Daubach and Darren Lewis hit back-to-back leadoff doubles in the fifth and the latter scored on Offerman's single two outs later to make it 8−0 Boston. 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. In the seventh, Nixon hit a leadoff single, moved to second on a groundout, and scored on Valetin's single. One out later, Garciaparra's home run made it 12−0 Boston. O'Leary then doubled to left and scored Boston's last run on Stanley's single. Martinez, for his part, pitched brilliantly, striking out twelve Yankees in seven scoreless innings and allowing just two hits. He would finish 1999 with a streak of seventeen scoreless innings in the playoffs. The Yankees scored their only run on Scott Brosius's home run off of Tom Gordon in the eighth. The Red Sox would go on to win 13–1 and make the series two games to one.
Sunday, October 17, 1999, at Fenway Park in Boston, Massachusetts
Game 4 pitted Andy Pettitte against Bret Saberhagen. The Yankees would score first after Darryl Strawberry hit a solo home run to silence the crowd chants of "Darryl, Darryl" and "Just say no" in his first at-bat. 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. Next inning Damon Buford hit a one out single, stole second and scored on Jose Offerman's single to put the Red Sox ahead 2–1. 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. The score remained the same until the Yankees blew the game open with six runs in the ninth. Chuck Knoblauch and Derek Jeter hit back-to-back one out singles off of Rich Garces, then an errant throw on Paul O'Neill's ground ball allowed Knoblauch to score. Williams's single scored Jeter before Martinez was intentionally walked. Rod Beck relieved Garces and allowed a grand slam to Ricky Ledée to cap the scoring at 9−2 Yankees. They were one win away from the World Series.
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. The blown call is now famously referred to as "The Phantom Tag".
Monday, October 18, 1999, at Fenway Park in Boston, Massachusetts
Game 5 was a rematch between Mercker and Hernandez. Chuck Knoblauch singled to lead off the first and Jeter followed with a home run to put the Yankees up for good. 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. Rheal 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. El Duque kept the Red Sox in check, allowing only one run on a homer by Jason Varitek in the eighth. The Yankees added insurance in the ninth on Williams's two-run home run off of Tom Gordon. Both teams left eleven men on base and the Yankees would go on to win the pennant.
1999 ALCS (4–1): New York Yankees over Boston Red Sox