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 series, 3-0.
- (2) Cleveland Indians (Central Division champion, 97–65) vs. (4) Boston Red Sox (Wild Card, 94–68): Red Sox win series, 3–2.
The higher seed (in parentheses) had the home field advantage (Games 1, 2 and 5 at home), which was determined by playing record. The Yankees played the Rangers, rather than the wild card Red Sox, because the Yankees and Red Sox are in the same division.
The Yankees rolled over the Rangers, who scored 945 runs in 1999, for the second straight year three games to none. 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.
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