Then. Based on the cars in the photo, I'd say mid-1950s.
From Retiring Guy's postcard collection
Now. No more angle parking. But room for outdoor seating.
Photo by Retiring Guy
Then. From the 1955 Madison City Directory.
Other Madison Then and Now posts:
Park Hotel/Inn on the Park, Madison Wisconsin. (9/8/2015)
U.S Post Office and Courthouse/Madison (WI) Municipal Building. (9/2/2015)
City-County Building. (9/1/2015)
Veterans Administration Hospital. (8/27/2015)
The Red Gym: When will the unobstructed view return? (7/22/2015)
UW-Madison College of Agriculture. (7/22/2015)
Wisconsin State Historical Society. (7/21/2015)
UW-Madison Memorial Union. (7/21/2015)
240 West Gilman. (9/6/2013)
North Carroll Street between West Johnson and West Gorham. (9/5/2013)
East Mifflin & North Pinckney. (8/30/2013)