By the 1920s, Winnipeg established a robust public education system that was a source of civic pride. Provincial regulations stipulating design requirements for school buildings helped further this along, as did the 1885 appointment of Danial McIntyre as both Inspector and Superintendent of the Winnipeg School District. McIntyre established a rapport with the Chairman of the Winnipeg School District’s Committee on Buildings, James Bertram Mitchell.

Together, the pair oversaw the creation of 50 school buildings. Wolseley School among them. This small one-storey building, designed by John Nelson Semmens, was meant to relieve the enrollment pressure of neighbouring schools. At the time of the school’s 1921 opening, there were only nine classrooms. Financial restraints led to limited ornamentation on the bungalow-style building. Lightly coloured stone contrasts nicely with the deep red brick walls and pointed arches cap the school’s two exterior doorways. Surrounding these arches are stone crests and decorative parapets.

A 1959 expansion added a kindergarten room, and general-purpose space. Of interest, the first four principals of Wolseley School were all women: Olive Maud McLean, Elizabeth Agnes Nicks, Dorothy Elanor Lane, and Frances Louise Martin.

In 2003, a larger renovation upgraded heating and ventilation systems, and added classroom space and services.