The Sporting Life #1: Rangers vs. Black Hawks, c. 1960s
I can’t be certain when this photo was taken, but I think that’s Glenn Hall wearing the #1 jersey for the Chicago Black Hawks. If so, this dates from 1967 or earlier.
I’m also fairly certain that I see Chico Maki wearing #16 for Chicago. I couldn’t even guess who the New York Rangers player is here.