In my time spent on google newspaper archives, I have come across some terrific sports themed cartoons in the old Montreal Gazette paper. These fantastic pieces of artwork were done by John Collins. Collins was one of Canada's greatest cartoonists and from 1941 to 1973 was the official cartoonist of The Gazette. As well as sports themed subjects he tackled all matter of national and international political events. During the hockey season, he did a hockey themed editorial cartoon every second day or so.
These ones are from the first few months of the 1949/50 NHL season and commonly depict the angle from a Montreal Canadiens view and their quest to supplant Toronto as the top team in the league.