When was the last time the Cubs played the Cards in the playoffs? For real? How about never That's kind of remarkable Not really. The Cubs have only made the playoffs 6 times and played in 7 playoff series in the 46 years since NL teams played each other in the playoffs And for 25 years they were in the same division and couldn't play each other in the playoffs. For an additional 16 years they could not face each other until the NLCS.