Earl Robertson traveled a long and winding path to the NHL that took him to a variety of cities and through a handful of leagues. He started out as a junior backstopper for the Regina Falcons in 1925-26. A couple of seasons later, he went to the West Coast to tend goal for the Vancouver Monarchs junior club and then turned pro with the Victoria Cubs of the PCHL in 1928-29.
The big leagues were still a long way off as he switched to the Tacoma Tigers of the PCHL in 1930-31. His stay with the club was short, however, as he headed south to play for the Oakland Sheiks and then the Hollywood Stars of the Cal-Pro League.
In 1932-33, Robertson returned to Canada to play goal for the Edmonton Eskimos of the WCHL. There, he performed consistently with a respectable goals-against average during his two campaigns with the club.
From 1934 to 1936, he played for the Windsor Bulldogs of the IAHL and seemed to only get better with experience. The Detroit Red Wings took notice of the goaltender's skills and purchased his rights from the Bulldogs. The Wings' brass tucked Robertson away with their minor-league affiliate in Pittsburgh for the start of the 1936-37 campaign. He put in a solid season and was rewarded with a shot in Detroit at the start of the playoffs. It must have been quite breathtaking for the netminder to progress from the Hollywood Stars to the Wings, play only six games with a stingy 1.41 goals-against average, and claim a Stanley Cup victory. It would never be any better for the aged rookie goalie.
But in spite of his success, Roberston was traded to the New York Americans shortly after the confetti from the victory parade had been swept up. The Amerks were a club that had their bright moments, but couldn't seem to get on track to win a championship. During his four seasons with the club, the Americans' fortunes only seemed to sag with time. By 1940-41, Robertson finished the season with a 6-22-8 record.
In 1941-42, his club became known as the Brooklyn Americans, but a change in name could do little to revive Robertson's fading career. He appeared in only 12 games before heading to the minors with the Springfield Indians where he retired at the close of the campaign.