100th Anniv pencil is from 1969, and McQuinn set is from 1938-1945 (his Browns playing days).
http://en.wikipedia.org/wiki/George_McQuinn
These sets were made for many teams and players throughout the 40's through 60's, and beyond. They where probably available at the stadiums to purchase as well. Fountain pen type probably from 30s and 40s, ballpoint types from 50s on.