The longest currently active MLB postseason series win drought belongs to the Cincinnati Reds, who have gone 25 years without winning a postseason series.
The longest all time MLB postseason series win drought belongs to the Chicago Cubs, who went 94 years without winning a postseason series between 1909 and 2003.
| Team | Years | Start Year |
|---|---|---|
| Cincinnati Reds | 25 | 1996 |
| Seattle Mariners | 19 | 2002 |
| Minnesota Twins | 18 | 2003 |
| Chicago White Sox | 15 | 2006 |
| Los Angeles Angels | 11 | 2010 |
| Philadelphia Phillies | 10 | 2011 |
| Texas Rangers | 9 | 2012 |
| Pittsburgh Pirates | 7 | 2014 |
| Detroit Tigers | 7 | 2014 |
| Baltimore Orioles | 6 | 2015 |
| New York Mets | 5 | 2016 |
| Kansas City Royals | 5 | 2016 |
| Cleveland Indians | 4 | 2017 |
| Toronto Blue Jays | 4 | 2017 |
| San Francisco Giants | 4 | 2017 |
| Arizona Diamondbacks | 3 | 2018 |
| Chicago Cubs | 3 | 2018 |
| Boston Red Sox | 2 | 2019 |
| Milwaukee Brewers | 2 | 2019 |
| Colorado Rockies | 2 | 2019 |
| St. Louis Cardinals | 1 | 2020 |
| Washington Nationals | 1 | 2020 |
| Team | Years | Start Year | End Year |
|---|---|---|---|
| Chicago Cubs | 94 | 1909 | 2003 |
| Chicago White Sox | 87 | 1918 | 2005 |
| Philadelphia Phillies | 77 | 1903 | 1980 |
| Baltimore Orioles | 63 | 1903 | 1966 |
| Minnesota Twins | 62 | 1925 | 1987 |
| Boston Red Sox | 56 | 1919 | 1975 |
| Brooklyn Dodgers | 52 | 1903 | 1955 |
| Texas Rangers | 49 | 1961 | 2010 |
| Cleveland Indians | 46 | 1949 | 1995 |
| Milwaukee Braves | 42 | 1915 | 1957 |
| Houston Astros | 42 | 1962 | 2004 |
| Oakland Athletics | 41 | 1931 | 1972 |
| Anaheim Angels | 41 | 1961 | 2002 |
| Washington Nationals | 37 | 1982 | 2019 |
| Pittsburgh Pirates | 34 | 1926 | 1960 |
| San Francisco Giants | 34 | 1955 | 1989 |
| Atlanta Braves | 33 | 1958 | 1991 |
| Pittsburgh Pirates | 33 | 1980 | 2013 |
| Detroit Tigers | 32 | 1903 | 1935 |
| Cincinnati Reds | 29 | 1941 | 1970 |
| Kansas City Royals | 28 | 1986 | 2014 |
| Milwaukee Brewers | 28 | 1983 | 2011 |
| Cleveland Indians | 27 | 1921 | 1948 |
| Cincinnati Reds | 25 | 1996 | |
| St. Louis Cardinals | 23 | 1903 | 1926 |
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