The riding of Winnipeg South was created in 1917 and changed hands many times between the Liberals and the Conservatives. The riding was represented by Liberal MP James Armstrong Richardson from 1968 to 1979. That year, Winnipeg South was dissolved and its geographical area redistributed into three different ridings.
In 1987, during another round of redistribution, the name Winnipeg South was given to a new riding formed from the dissolved ridings of Winnipeg Assiniboine and Winnipeg Fort Garry. Conservative MP Dorothy Dobbie was the first MP to represent the new riding.
Liberal MP Reg Alcock defeated Dobbie in 1993, representing Winnipeg South until 2006, when he was defeated by the Conservative MP Rod Bruinooge, who has represented the riding in Ottawa since then.
In 2008, Liberal candidate John Loewen led an unsuccessful campaign against Bruinooge, losing by approximately 5,700 votes.
The Liberal candidate for Winnipeg South in the 2011 federal election was former Winnipeg City Councilor, Executive and Environmental Scientist, Terry Duguid.
On October 19, 2015 Terry Duguid was elected the Member of Parliament for Winnipeg South, winning the election with over 28,000 votes or 58% of the popular vote.