The history of the cathedral in Winnipeg dates back to the beginning of the 20th century when, on September 1, 1907, a parish was founded by the decision of the assembly of the faithful and in the presence of Fr. Mykola Strutynsky.

On December 27, 1912, in the original church of Saints Volodymyr and Olha, which stood on the site of the current metropolitan cathedral, the first bishop for Ukrainians in Canada, Blessed Nykyta Budka, celebrated the first Hierarchal Divine Liturgy. Later, on April 25, 1913, he elevated the church to the dignity of a pro-cathedral.

On March 1, 1920, the parish purchased 28 acres (11.33 hectares) of land for the All Saints Cemetery in West St. Paul, which Bishop Nykyta Budka consecrated on June 13, 1920.

During its more than a century-long history, the cathedral has been visited by leaders of the Ukrainian Catholic Church. For example, on September 5, 1921, during his second pastoral visit to Canada, Metropolitan Andrey Sheptytsky visited the shrine.

In 1926, the church was rebuilt, with a large dome erected.

In 1948, construction began on a new (current) church, which, according to the decision of the Apostolic See, was to become a cathedral in the future. On September 26, 1948, Archbishop Vasyl Ladyka consecrated the cornerstone for the construction of the new shrine. The official opening of the new church of Saints Volodymyr and Olha in Winnipeg took place on April 15, 1951 (the consecration, however, did not take place until 1977). It was performed by Archbishop Ladyka in the presence of Cardinal James Charles McGuigan of Toronto.

Shortly after the opening of the church, a new stage in the history of the Ukrainian Catholic Church in Canada began. On November 3, 1956, Pope Pius XII created the Winnipeg Metropolia, and the church of Saints Volodymyr and Olha became a metropolitan cathedral. On February 12, 1957, Bishop Maxim Hermaniuk was enthroned in the cathedral as the first metropolitan of Winnipeg and all Canada.

The successor of Metropolitan Andrey Sheptytsky, Patriarch Yosyf Slipyj, first visited this cathedral on June 21, 1968, celebrating the Hierarchical Divine Liturgy there. Later, in April 1973, Patriarch Yosyf also led the Easter Liturgy here. He visited the cathedral parish for the third time in 1976.

Blessed Vasyl Velychkovskyy also celebrated the Hierarchical Liturgy in the church, first on July 2, 1972.

The consecration of the cathedral and the main altar took place on June 12, 1977. It was performed by Metropolitan Maxim Hermaniuk. During the consecration, Metropolitan Hermaniuk placed the relics of Saint Josaphat Kuntsevych in the altar.

On September 16, 1984, the Cathedral of Saints Volodymyr and Olha was visited by Saint Pope John Paul II, who consecrated a monument to Saint Volodymyr the Great in its courtyard.

In June 1986, the Hierarchical Divine Liturgy was celebrated here by the Major Archbishop Myroslav Ivan Cardinal Lubachivsky.

On November 22, 1988, Metropolitan Maxim Hermaniuk celebrated the Hierarchical Divine Liturgy of Thanksgiving in the cathedral on the occasion of the 50th anniversary of his priesthood.

Episcopal ordinations have been held in the metropolitan cathedral. On June 13, 1996, Bishop Stefan Soroka, named Auxiliary Bishop of Winnipeg, was consecrated here. On June 11, 2002, the episcopal ordination of Bishop David Motiuk, named Auxiliary Bishop of Winnipeg, took place in the cathedral. And on February 11, 2006, the enthronement of Archbishop and Metropolitan of Winnipeg Lawrence Huculak took place. The most recent ordination took place on November 8, 2023, when Metropolitan Lawrence Huculak, along with Metropolitan of Philadelphia Borys Gudziak and Eparch of Edmonton David Motiuk, consecrated Bishop Michael Kwiatkowski, named Eparch of New Westminster.

From September 9-15, 2012, the Synod of Bishops of the UGCC was held in Winnipeg, coinciding with a celebration of the arrival of the blessed Hieromartyr Nykyta Budka to Canada. On this occasion, the Father and Head of the UGCC, His Beatitude Sviatoslav Shevchuk, joined by members of the Synod of Bishops, celebrated the Hierarchical Divine Liturgy in the cathedral.

The number of faithful has grown over the years. At the time of the founding of the parish, there were 45 members. By 1941, this number had increased to 350, and by the 1980s, it had reached 800.