Sidney Diamond was a graduate of St. John's Technical High School. After serving as a Corporal in the Canadian army (during World War II) he graduated from the university of Manitoba, Faculty of Architecture. He registered with the Manitoba Association of Architects in October 1955. Diamond was a partner in the firm of Libling Michener Diamond during the mid-century period. Subsequently, in the 1960s and 70s, Diamond was an Instructor at Moose Jaw Technical Institute. He passed away in 1985.