In the 1950s, 1960s and early 1970s, the two teams played an annual exhibition series, which I detailed in this 2012 article:
After World War II, the teams played an annual in-season exhibition game called the “Boys Benefit Game,” with proceeds to boys’ baseball teams in Chicago. These matches alternated years in old Comiskey Park and Wrigley Field; the Cubs, though by far the worse team in the 1949-72 time frame these games were played, won the series 13-10. (They skipped 1950, since the White Sox hosted the All-Star Game that year.)
I was sent the link to this video Friday, a remarkable three and a half minute home movie of one of those games:
Whoever shot this film clearly had either access to the field or a front-row seat, because there are closeups of a lot of both Cubs and White Sox players.
So, what year is this? Well, you can see the teams’ managers, Leo Durocher and Eddie Stanky. That narrows it down immediately — the only years both those men managed in Chicago at the same time were 1966 and 1967. Durocher and Stanky were longtime friends, as Durocher had managed Stanky with the Dodgers from 1944-46 and again with the Giants in 1950 and 1951. Stanky also played for the Cubs in 1943 and 1944.
Among the Cubs players you can see in this film are Joe Amalfitano (No. 5), Paul Popovich (No. 22), Ron Santo (No. 10), Ernie Banks (No. 14), Randy Hundley (No. 9) and Cal Koonce (No. 34).
The clincher as to which year this was is at 1:25 of the video. No. 11 of the White Sox is Jimmy Stewart. Not the actor, Stewart had played for the Cubs beginning in 1963 until he was sold to the White Sox May 22, 1967.
The Cubs/White Sox Boys Benefit Game that year was played exactly a month later, Thursday, June 22, 1967 at Comiskey Park, so Stewart’s former Cubs teammates were catching up with him.
39,443 paid to see this exhibition game, which, per Tribune writer Edward Prell, raised over $83,000 for boys baseball in Chicago. (That’s the equivalent of about $655,000 today.)
The Sox won the game 2-0. Koonce started for the Cubs and allowed one run in five innings, then was relieved by Rob Gardner, who allowed the other Sox run. All 15 hits in the game (10 by the Sox, five by the Cubs) were singles, emblematic of that era, one dominated by pitchers. Banks, Santo, Adolfo Phillips, John Boccabella and Norm Gigon accounted for the Cubs hits. Gigon played in just 34 games for the Cubs in 1967, his only big-league season, but later became a significant footnote in franchise history. He was Joe Maddon’s baseball coach at Lafayette College.
As noted, these charity games ended after 1972, largely because it was becoming more difficult to schedule them. The last Cubs in-season exhibition game was played against a team of Southern League All-Stars in 1996, which you can read about here.