Unraveling MLB’s Longest Postseason Dry Spells: Which Teams Are Doomed to Wait Forever?
2. Cleveland, 40 Seasons (1955-94)
We return once again to Cleveland, which, after getting swept by the New York Giants in the 1954 World Series, wouldn’t return to postseason baseball until 1995. In fact, the team didn’t even finish in second place in its own division until after MLB had split each league into three divisions ahead of the 1994 season – and that season was stopped midway through the year due to a strike by the MLB Players Association.
T-3. Oakland Athletics, 39 Seasons (1932-70)
T-3. Chicago White Sox, 39 Seasons (1920-58)
Longest Playoff Series Win Droughts – All Time
1. Chicago Cubs, 94 Seasons (1909-2002)
For obvious reasons, this could not have been any other franchise. The Cubs went the longest without a World Series appearance (see below) or a World Series win (see above), so they could not have possibly won a series in between those years. Even after MLB introduced the wild card in 1995, the Cubs still got swept by the Braves in 1998. Finally, in 2003, the Cubs defeated the Braves in five games in the NLDS, winning their first postseason series since winning the World Series in 1908.
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