First, here’s a look at the full photo, which has quite a bit of detail of the Clark Street area surrounding Wrigley Field:
You can clearly see the rail line that used to run next to Wrigley, including a crossing gate.
The marquee says the Cubs were hosting the Phillies on May 3, 4 and 5, so it was a simple matter of finding dates that matched. The car is a clue, that’s a car from the late 1930s or early 1940s, and that’s exactly where I found the exact dates.
The dates match a series the Cubs played against the Phillies in Wrigley Field in 1938. There aren’t any people around, except for the man near the crossing gate and a few others on the corner of Clark & Addison, so I’d say this photo was probably taken the day before the series began, which would have been Monday, May 2, 1938.
The Cubs won two of three in that set, defeating the Phillies 5-2 on May 3, losing 6-4 on May 4 and crushing the visitors 21-2 on May 5. The Cubs, of course, won the National League pennant that year and the Phillies were execrably awful, finishing 45-105, the first of five straight years they’d lose 100 games or more. Interestingly, their manager that year, Jimmie Wilson, would become Cubs manager from 1941-43. Wilson was fired 10 games into the 1944 season with a 1-9 record.
The photo has some good detail of the exterior of the ballpark from that era and you can clearly see how the 1060 Project did a good job of replicating the ironwork that existed at Wrigley in the 1930s.
Just another slice of Cubs history, now from nearly 85 years ago.