It is unfathomable that the Cubs have never clinched a playoff series win at Wrigley but, you know, Cubs.
I also never realized they have only won ONE playoff series since 1908: the 2003 NLDS.
Yup - they haven't had all that many chances recently, but they lost 7 world series between 1910-1945. Divisional play began in 1969...before that, the only "postseason series" was the World Series. For many of these years, the owners didn't give a crap about winning. Also, they've only had the NLDS since about 1996?
Divisional Playoff appearances:
1984
1989
1998
2003
2007
2008
2015
They were within 1 game of the world series in 1984 and 2003 (and had 2 game series leads in both). Excluding those years and 2015, they only have 1 playoff win. They were swept in 1998, 2007, 2008 and only won a single game in the 1989 NLCS.