The land around what would later become Grant Park Shopping Centre was first developed with the introduction of the Harte Subdivision for the Grand Trunk Pacific Railway in 1908.

[2][3] From the 1920s to late 1950s, the Grant Park area was the location of a Métis community known as Rooster Town.

[6][7] Rooster Town has been described by Lawrie Barkwell, senior historian at the Louis Riel Institute, as a "working-class community with a vibrant culture.

The centre opened with a few detached buildings in 1964; some of the original stores included Safeway, Dominion, and Clarke’s.

[11][2] With the Court ruling in favour of Woolco, efforts began to enclose the mall in order to connect stores together.

Further renovations in the mid-1990s made for the opening of Winnipeg's largest McNally Robinson Bookseller location in order to compete with the Chapters retail chain.

[19] 2 new pad sites were built on the lot during 2016-2017; Cambrian Credit Union and Fionn MacCool's Pub.