The 1999 American League Division Series (ALDS), the opening round of the 1999 American League playoffs, began on Tuesday, October 5, and ended on Monday, October 11, with the champions of the three AL divisions—along with a "wild card" team—participating in two best-of-five series. The teams, which were identical to those qualifying in 1998, were:

(1) New York Yankees (Eastern Division champion, 98–64) vs. (3) Texas Rangers (Western Division champion, 95–67): Yankees win the series, 3–0. (2) Cleveland Indians (Central Division champion, 97–65) vs. (4) Boston Red Sox (Wild Card, 94–68): Red Sox win the series, 3–2.

1999 American League Division Series

The Yankees rolled over the Rangers, who scored 945 runs in 1999, for the second straight year three games to none, conceding only one run total in the series also for the second year in row. The Red Sox battled back down two games to none against a Cleveland Indians team that was the first to score 1,000 runs in a season in nearly 50 years and won the Series three games to two, thanks to Pedro Martínez. The Yankees would go on to defeat the Red Sox four games to one in their first-ever meeting in the postseason in the AL Championship Series, and would then go on to sweep the National League champion Atlanta Braves in the 1999 World Series.

1999 American League Division Series

Matchups

New York Yankees vs. Texas Rangers

Cleveland Indians vs. Boston Red Sox

New York vs. Texas

Game 1

Yankee Stadium (I) in Bronx, New York

The Yankees once again swept the Rangers and held them to one run through three games. In Game 1, Aaron Sele went against Orlando Hernández. Ricky Ledee's RBI double in the second innings put the Yankees up 1–0. In the fifth, innings Derek Jeter and Paul O'Neill hit back-to-back two-out doubles before both scored on the Bernie Williams's double. Next inning, Ledee and Jeter walked off Sele and the reliever Tim Crabtree respectively before Texas third baseman Todd Zeile's error on O'Neill's ground ball allowed Ledee to score off Mike Venafro before Williams's three-run home run made it 7–0. Williams got his sixth innings RBI of this game with a single in the eighth off Jeff Fassero that scored Chuck Knoblauch. Jeff Nelson relieved Hernandez in the ninth.inning and pitched a scoreless inning to seal the Yankees' 8–0 win.

1999 American League Division Series

Game 2

Yankee Stadium (I) in Bronx, New York

In Game 2, Rick Helling went against Andy Pettitte. Juan González gave the Rangers the lead with a home run in the fourth. This would be the lone run in the series for the Rangers, who scored 945 runs in 1999. Scott Brosius's double tied the game in the bottom of the fifth. Ricky Ledée's RBI double gave the Yankees the lead in the seventh. In the bottom of the eighth, the Yanks got an insurance run when Mike Venafro walked Jim Leyritz with the bases loaded, scoring Chad Curtis. Mariano Rivera retired the side in order for the Game 2 save.

Game 3

The Ballpark in Arlington in Arlington, Texas

In Game 3, the Yankees took an early lead when Darryl Strawberry hit a three-run home run off Esteban Loaiza in the first inning. Roger Clemens pitched seven innings and allowed only three hits. Mariano Rivera got the series-winning save in the ninth inning. For the second consecutive year, the Yankees completed a three-game sweep of the Rangers while holding them to one run of offense in the series.

Composite box

1999 ALDS (3–0): New York Yankees over Texas Rangers

Cleveland vs. Boston

Game 1

Jacobs Field in Cleveland, Ohio

Boston jumped out to an early 1–0 lead with a lead-off home run by Nomar Garciaparra in the second inning off Indians' starter Bartolo Colón. Garciaparra set up the second run for the Red Sox when he led off the fourth inning with a double and then scored on an RBI single by Mike Stanley. Facing Cy Young Award winner Pedro Martínez, the Indians looked to be in serious trouble, but the ace of the Red Sox pitching staff left the game due to injury in the bottom of the fifth inning and was replaced by Derek Lowe. The Indians would tie the game in the bottom of the sixth with a two-run home run by Jim Thome, and Colón settled down and dominated the Red Sox hitters the rest of the way, striking out 11 in eight innings pitched. In the bottom of the ninth, the Indians handed Lowe a "L", walking the game off when Travis Fryman hit a game-winning single off Rich Garces with the bases loaded.