The football career of Cliff Roseborough began in Saskatoon with Bedford Road Collegiate. Upon graduating he played with the Hilltops until 1932 when he played for Al Ritchie’s powerhouse Regina Roughriders. The Riders lost the Grey Cup Final in 1932 and the Western Final to Winnipeg in 1933. Roseborough joined Carl Cronin’s Winnipegs the following year, only to lose to his former mates in the West title game. He would obtain a measure of revenge when Bob Fritz took over the coaching reins in Winnipeg and led the team to the west’s first ever Grey Cup in 1935. Roseborough would taste victory again in the Dominion final in 1939 and 1941 under coach Reg Threlfall. He retired as a player in 1942 and began his second career in football in earnest.
During his playing days Roseborough officiated at the high school and junior levels in Winnipeg. He helped found the Manitoba Officials Association with fellow inductee Bert Warwick, and served as its President on five occasions between 1936-50. From 1934 until retiring as an official in 1964, Roseborough added the Western Inter-Provincial Rugby Union to his resume and when he refereed his first of 12 Grey Cup games, he was the first official from Western Canada to do so. Cliff Roseborough also served as President of the Winnipeg Blue Bomber Alumni Association in 1958 and again in 1965, the year in which the team celebrated the 30th Anniversary of the West’s first Grey Cup championship.