​The Chicago Cubs are celebrating their 150th anniversary this year. The Chicago White Sox, charter members of the American League in 1901, are in their 126th season.That’s a lot of baseball and a lot of history. And in the World Series era of Major League Baseball the two Chicago teams have played in October in the same year in just three of the 121 seasons we’ve had postseason baseball. Those years are 1903 to 2025, with these exceptions: 1904 (no World Series because manager John McGraw of the Giants was being pigheaded and refused to play the AL champion A’s) and 1994, when the postseason was cancelled due to a players’ strike.AdvertisementAdvertisementAdvertisementIn addition to having been in the postseason together just three times, the Cubs were often awful when the Sox were in the postseason and vice versa. Consider this article a slice of Chicago baseball history.I’ve made two tables to show that to you. First, here are the 22 Cubs postseason years:YearCubs record/finishWhite Sox record/finish1906116-36, NL pennant93-58, WS champions1907107-45, WS champions87-64, third place190899-55, WS champions88-64, third place1910104-50, NL pennant68-85, sixth place191884-45, NL pennant57-67, sixth place192998-54, NL pennant59-93, seventh place193290-64, NL pennant49-102, seventh place1935100-54, NL pennant53-99, eighth place193889-63, NL pennant65-83, sixth place194598-56, NL pennant71-78, sixth place198496-65, NL East title74-88, fifth place198993-69, NL East title69-92, seventh place199890-73, NL Wild Card80-82, second place200388-74, NL Central title86-76, second place200785-77, NL Central title72-90, fourth place200897-64, NL Central title89-74, AL Central title201597-65, NL Wild Card Game winner76-86, fourth place2016103-58, WS champions78-84, fourth place201792-70, NL Central title67-95, fourth place201895-68, NL Wild Card Game loser62-100, fourth place202034-26, NL Central title35-25, AL Wild Card series loser202592-70, NL Wild Card Series winner60-102, fifth placeWhile the Cubs were good in the 1920s, 1930s and 1940s, the Sox were pretty bad for almost that entire era. Here’s the chart for the 11 White Sox postseason years:YearWhite Sox record/finishCubs record/finish190693-58, WS champions116-36, NL pennant1917100-54, WS champions74-80, fifth place191988-52, AL pennant75-65, third place195994-60, AL pennant74-80, fifth place198399-63, AL pennant71-91, fifth place199394-68, AL West title84-78, fourth place200095-67, AL Central title65-97, sixth place200599-63, WS champions79-83, fourth place200889-74, AL Central title97-64, NL Central title202035-25, AL Wild Card series loser34-26, NL Central title202193-69, AL Central title71-91, fourth placeApart from the three matching postseason years, the Cubs were also generally pretty bad when the Sox played in October, most recently in 2021 when the Sox appeared to have a team that could make the playoffs in multiple years and the Cubs had their big selloff. That postseason run for the S