In 1925, Robertson started his long journey with the Regina Falcons of the Saskatchewan Junior League, playing in eight games and compiling a 4-3-0 record, which going 0-2 in the playoffs, and 0-2 again in the Memorial Cup Finals. The 1926-27 had Robertson stay in Regina, playing six games with a 4-2-0 record, as well as losing his only playoff games. Robertson moved to Vancouver to their Senior League playing for the Vancouver Monarchs in the 1927-28 season, finishing with a 4-2-2 record in eight games, while also going 1-2-1 in four Allan Cup games.
Finally getting out of the amateur ranks, Robertson joined the Pacific Coast League in the 1928-29 season for the Victoria Cubs, compiling a 7-21-6 record for 34 games. Robertson played 31 games in the 1929-30 season and another 10 games for the Tacoma Tigers in the 1930-31 season; but no records are available for those years. Also in the 1930-31 season, Robertson went to the California Pro League, playing and winning his one game with the Oakland Sheiks. Staying in the California League in the 1931-32 season, but playing for the Hollywood Stars; Robertson went 20-7-4 in 31 games before moving along again. Robertson joined the Edmonton Eskimos of the Western Canadian/Northwest Leagues for the 1932-33 and 1933-34 seasons for a total of 60 games, compiling 10 shut-outs, but no win-loss records are available.
After dealing out west, Robertson moved to the Windsor Bulldogs of the International League for the 1934-35 season, playing in 40 games and finishing with a 14-19-7 record; while in the 1935-36 season, Robertson improved himself with an 18-19-11 record with the Bulldogs, as well as an 0-2-0 record with the Rochester Cardinals of the IHL that same season.
In a world of inter-league trades, the Bulldogs traded Robertson to the NHL's Detroit Red Wings for cash before the 1936-37 season, to which the Red Wings would sent Robertson back to the IHL and the Pittsburgh Hornets-- where he would go 14-15-0 in 29 games. However, Robertson's shining moment would come in the 1937 Stanley Cup Finals, where he was called into duty to fill in for the injured Normie Smith. Robertson went 4-2 in the playoffs, helping the Red Wings to their second-straight Stanley Cup championship. Robertson also holds the distinction of stopping the first penalty shot given in the Stanley Cup playoffs.
Though, the celebration was short lived, as Robertson was on the move again-- this time to the New York Americans for John Doran and cash. Robertson got thrown into the starting role for the Americans in the 1937-38 season, playing in 48 games and compiling a 19-18-11 record and 3-3 in six playoff games, while the 1938-39 season yielded a 17-18-10 record in 46 games. The 1939-40 season was a dismal one for Robertson, going 15-29-4 in 48 games, while going 1-2 in three playoff matches.
Robertson came to a cross-roads starting in the 1940-41 season, playing in 36 games for the Americans and going 6-22-8, before he was sent to the AHL's Springfield Indians, posting a 4-5-2 record in 11 games and 1-2 in the playoffs. While the Americans moved to Brooklyn in the 1941-42 season, Robertson didn't spend much time there-- playing only 12 games in the NHL (3-8-1) before settling in at the AHL level with Springfield, finishing there with a 24-14-3 record in 41 games down there, then 2-1 in three playoff games.
After sitting out the 1942-43 season, Robertson played the 1943-44 season with the Edmonton Vics of the Senior Leagues, though Robertson would only play in exhibition games and three Allan Cup games, where he would lose all three before retiring for good. Robertson passed on in 1979 at the age of 67. In 2008, Robertson was inducted into the Wetaskiwin and County Sports Hall of Fame in Wetaskiwin, Alberta.
It was a long strange trip for Robertson, showing him every aspect of hockey life and pretty much every part of the globe in a time where hockey wasn't as popular as it is today. When he finally made the show, Robertson had the highest high-- but then suffered struggling seasons afterwords and then flamed out it would seem. Even so, all the travels didn't deter Robertson from his dream, which he got and did what few could-- a Stanley Cup.
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