The Cubs could close out the regular season this weekend at Milwaukee, then begin the playoffs there as well.
Has any team done that in any previous season?
To find the answer, I examined the final series of every first-round playoff qualifier for every season since 1969, first year of division play.
I uncovered just 6 times that it has happened:
The first 2 were in 1981, a season interrupted by a strike, after which all teams began 0-0 again, then the first-half and second-half leaders in the league's 2 divisions squared off to begin the post season.
In the American League, the Athletics won 2 of 3 at Kansas City to end the regular season, then swept the Royals in 3 games in the playoff series.
In the National, the Dodgers won 2 of 3 at home against the Astros, then won the playoff rematch, 3 games to 2.
The Twins lost 2 of 3 at home to the Blue Jays to finish 1991, but won 4 of 5 in the playoffs.
In 2013, the Pirates swept 3 games at Cincinnati, then returned home and beat the Reds in the Wild Card game.
In 2017, the Astros won 3 of 4 at Boston, then did the same against the Red Sox in the post season.
In 2018, the Red Sox lost 2 of their 3 final games at home against the Yankees, then went 3-1 in the playoffs.
CUBS AND PLAYOFF FOES
The latest in the regular season that the Cubs faced any of their post-season opponents was in 2015, when they hosted the Pirates on Sept. 25-27, in games 153-155 of their schedule.
The Cubs then won a makeup home game at home against the Royals and swept series at Cincinnati and Milwaukee before going to Pittsburgh, where they beat the Pirates, 4-0, in the Wild Card game on Oct. 7.
Here are each year in which the Cubs made the playoffs, their first-round opponent, the latest dates on which they played the opponent in the regular season, where those games were played and the number of those games in the season:
1984: Padres, July 2-4, on road (78-80)
1989: Giants, July 21-23, at home (95-97)
1998: Braves, July 20-21, on road (98-99)
2003: Braves, July 21-22, on road (98-99)
2007: Diamondbacks, Aug. 24-26, on road (127-129)
2008: Dodgers, June 5-8, on road (61-64)
2015: Pirates, Sept. 25-27, at home (153-155)
2016: Giants, Sept. 1-4, at home (133-136)
2017: Nationals, Aug. 4-6, at home (108-110)
2018: Rockies, April 30-May 2, at home (26-28)
2020: Marlins, did not play in 60-game schedule due to pandemic