1999 Major League Baseball postseason
| Tournament details | |
|---|---|
| Dates | October 5–27, 1999 |
| Teams | 8 |
| Final positions | |
| Champions | New York Yankees (25th title) |
| Runners-up | Atlanta Braves |
| Tournament statistics | |
| Most HRs | Three tied (4) |
| Most SBs | Rickey Henderson (NYM) (7) |
| Most Ks (as pitcher) | Orlando Hernández (NYY) (27) |
| Awards | |
| MVP | Mariano Rivera (NYY) |
The 1999 Major League Baseball postseason was the playoff tournament of Major League Baseball for the 1999 season. The winners of the League Division Series would move on to the League Championship Series to determine the pennant winners that face each other in the World Series.
In the American League, the New York Yankees and Cleveland Indians returned to the postseason for the fifth straight time, and the Boston Red Sox and Texas Rangers returned for the second year in a row. This was Texas’ last postseason appearance until 2010.
In the National League, the Atlanta Braves made their eighth straight postseason appearance, the Houston Astros made their third straight appearance, the New York Mets made their first appearance since 1988, and the Arizona Diamondbacks made their postseason debut two years into their existence.
The postseason began on October 5, 1999, and ended on October 27, 1999, with the Yankees sweeping the Braves in the 1999 World Series. It was the Yankees' 25th title, which made them the team with the most championship wins in North American sports, surpassing the NHL’s Montreal Canadiens who won 24.
The 1998-99 Yankees were the last team to win back-to-back championships (that was not part of a three-peat) until the Los Angeles Dodgers did so in 2024 and 2025.