Agree with Jason..but I'll say the three oldest are probably pretty close in age. I have a "Los Angeles" Rams version of the small one and the Rams didn't move to L.A. until 1946. The stiff arm RB and the punter style were used pretty commonly for AAFC football pennants and defunct NFL teams (Boston Yanks, New York Yanks) from the 1940s and early 50s. The AAFC existed from 1946-49. The Boston Yanks from 1944-48. The New York Yanks 1950-51.
Interesting to note (to me anyway) the punter graphic made a comeback with Trench in the early 1960s. I've seen Cowboys, Raiders, Packers examples, with the Cowboys and Raiders not existing until 1960. But these are distinctive, because the flags around the stadium look like flags now...compared to the 1940s version (Marc's), in which the flags look like star blobs. All of the 1940s pennants have flags like this.
1940s version (star blob flags)
1960s version (normal flags)
