The sleuthing image you see above is from this tribute to WGN’s years televising the Cubs, posted on YouTube in 2019:
Just so you don’t have to go through the entire video to see where I found it, here are the three seconds’ worth of video where I made the screenshot above:
Now, let me tell you how I sleuthed not only the exact date, but the exact at-bat and time of day we are looking at.
The key to this one is not the scoreboard or the action on the field, it’s the two buildings at the top right of the photo.
That’s 3600 N. Lake Shore Drive, two buildings at the northwest corner of Addison and Lake Shore Drive.
Per an article in the Tribune, there was a topping-off ceremony for the construction of those buildings on May 11, 1960 (in fact, high winds forced the ceremony to move indoors). Construction on those buildings began, per the same article, April 22, 1959.
Thus, the buildings could not have been in this state of completion in 1959. This has to be early in the 1960 season. There are only three games with attendance that large at Wrigley before May 11 that year: The opening series against the Giants, April 22-23-24.
Consulting the results from those three dates, there were no night games on April 23 or 24. That means this has to be from Friday, April 22, 1960 (in fact, this was the home opener that year), and the board confirms that. There’s one night game on the AL side, that matches what we see. It’s hard to tell but if you squint real good, you can see NITE GAME across all the other games on the NL side, which matches what happened on that day.
Further evidence: On April 22, 1960, the White Sox/Detroit game (the one at the top on the AL side) started at 12:30 p.m. Central time. We see maybe three or four innings posted. The other AL game with innings posted is the score on the bottom. That’s got to be BALTIMORE/NEW YORK, I confirmed that game’s starting time was 1 p.m. Central (per the New York Times). Two innings or so are posted there. The other day game on the AL side is CLEVELAND/KANSAS CITY, no score is posted for that one.
Now, to the Cubs game. The scoreboard clock shows one hand on the 9, it is very likely 1:45 p.m. Weekday games at Wrigley in 1960 started at 1:30. The Cubs are in the field. Glen Hobbie, a righthander, started that game. There is no batter on the board, so he must have just stepped in to start the top of the second inning. It’s Orlando Cepeda. He grounded out to third base in that plate appearance. That’s what we are looking at in the brief video clip and the screenshot.
April 22, 1960 was an important day in WGN’s Cubs history, the first game they broadcast in color from Wrigley. That’s probably a reason we have this surviving video from more than 60 years ago, even though it’s in black and white.
The Cubs led this game 8-7 going into the eighth inning but wound up losing 10-8. The 1960 Cubs weren’t very good that year, going 60-94. The Giants finished fifth at 79-75, 16 games behind the pennant-winning Pirates.