Winnipeg lies at the confluence of the Assiniboine River and the Red River, which is known as The Forks, a historic focal point on canoe river routes travelled by aboriginal peoples for thousands of years. The name Winnipeg is a transcription of a western Cree word meaning "muddy waters".

In 1738, the Sieur de la Vérendrye built the first trading post on the site (Fort Rouge) which was ultimately abandoned. Other posts were built in the Red River region. Fort Gibraltar was built by the North West Company in 1809 and Fort Douglas was built by the Hudson's Bay Company (HBC) in 1812. The two companies fought fiercely over trade in the area with each destroying the other's fort over the course of several battles. In 1821, Hudson's Bay and North West Companies ended their long rivalry with a merger.

Fort Gibraltar, the site of present-day Winnipeg, was renamed Fort Garry in 1822 and became the leading post in the region for the Hudson’s Bay Company. Fort Garry was destroyed in an 1826 flood, and rebuilt in 1835. It played a small role in fur trading, but remained the residence of the Governor of the company for many years.In 1869 to 1870, Winnipeg was the site of the Red River Rebellion, a conflict between the local provisional government of Métis leader Louis Riel and newcomers from eastern Canada. This rebellion led directly to Manitoba's entry into Confederation as Canada's fifth province in 1870. On November 8, 1873, Winnipeg was incorporated as a city. In 1876, the post office officially adopted the name "Winnipeg," three years after the city's incorporation

The first locomotive in Winnipeg, the Countess of Dufferin, arrived via steamboat in 1877. The Canadian Pacific Railway completed the first direct rail link from Eastern Canada in 1881, opening the door to mass immigration and settlement of the Canadian Prairies. The history of Winnipeg's rail heritage and the Countess of Dufferin may seen at the Winnipeg Railway Museum.

Winnipeg experienced a boom during the 1890s and the first two decades of the twentieth century, and the city's population grew from 25,000 in 1891 to more than 179,000 in 1921. Immigration increased during this period and Winnipeg took on its distinctive multicultural character. The Manitoba Legislative Building reflects the optimism of the boom years. Built of Tyndall Stone and opened in 1920, its dome supports a bronze statue finished in gold leaf titled "Eternal Youth and the Spirit of Enterprise" but commonly known as the "Golden Boy". The Legislature was built in the neoclassical style that is common to many other North American state and provincial legislative buildings of the nineteenth and early twentieth centuries.

Winnipeg faced financial difficulty when the Panama Canal opened in 1914. The canal reduced reliance on Canada's rail system for international trade, and the increase in ship traffic helped Vancouver surpass Winnipeg to become Canada's third-largest city in the 1920s.

As a result of appalling labour conditions following World War I, 35,000 Winnipeggers walked off the job in May 1919, in what came to be known as the Winnipeg General Strike of 1919. The government broke the strike through arrests, deportation and violence. The strike ended June 21, 1919, when the Riot Act was read and a group of Royal Canadian Mounted Police (RCMP) officers charged a group of strikers; two strikers were killed and at least thirty others were injured, resulting in the day being known as Bloody Saturday. The lasting effect was a polarized population. One of the leaders of the strike, J.S. Woodsworth, went on to found Canada's first major socialist party, the Co-operative Commonwealth Federation (CCF), which would later become the New Democratic Party.

The stock market crash in 1929 only hastened an already steep decline in Winnipeg. The Great Depression resulted in massive unemployment, which was worsened by drought and depressed agricultural prices.

The Depression ended when World War II broke out in 1939. Thousands of Canadians volunteered to join the forces. In Winnipeg, the old established armouries of Minto, Tuxedo (Fort Osborne) and McGregor were so crowded that the military had to take over other buildings to increase capacity.

Winnipeg played a large part in the British Commonwealth Air Training Plan (BCATP). The mandate of the BCATP was to train flight crews away from the battle zone in Europe. Pilots, navigators, bomb aimers, wireless operators, air gunners, and flight engineers all passed through Winnipeg on their way to the various air schools across Western Canada. Winnipeg served as a headquarters for Command No. 2.

The end of World War II brought a new sense of optimism in Winnipeg. Pent-up demand brought a boom in housing development, but the building activity came to a halt due to the 1950 Red River Flood, the largest flood to hit Winnipeg since 1861. The flood held waters above flood stage for fifty-one days. On May 8, 1950, eight dikes collapsed and four of the city's eleven bridges were destroyed. Nearly 70,000 people had to be evacuated. Premier Douglas Campbell called for federal assistance and Canadian Prime Minister Louis St. Laurent declared a state of emergency. Soldiers from the Princess Patricia's Canadian Light Infantry regiment staffed the relief effort for the duration of the flood. The federal government estimated damages at over $26 million, although the province insisted it was at least double that.

To prevent future floods, the Red River Basin Investigation recommended a system of flood control measures, including multiple diking systems and a floodway to divert the Red River around Winnipeg. This prompted the construction of the Red River Floodway under Premier Dufferin Roblin 

Prior to 1972, Winnipeg was the largest of thirteen cities and towns in a metropolitan area around the Red and Assiniboine rivers. Unicity was created on July 27, 1971 and took effect with the first elections in 1972. The City of Winnipeg Act incorporated the current city of Winnipeg: the municipalities of St. James-Assiniboia, St. Boniface, Transcona, St. Vital, West Kildonan, East Kildonan, Tuxedo, Old Kildonan, North Kildonan, Fort Garry, and Charleswood were amalgamated with the Old City of Winnipeg.

In 1979, the Eaton's catalogue building was converted into the first downtown mall in the city. It was called Eaton Place but would change its name to Cityplace following the controversial demolition of the empty Eaton's store in 2002.

Immediately following the 1979 energy crisis Winnipeg experienced a severe economic downturn in advance of the early 1980s recession. Throughout the recession, the city incurred closures of prominent businesses such as the Winnipeg Tribune and the Swift's and Canada Packers meatpacking plants.

In 1993, feeling that their community needs were not being fulfilled, the residents of Headingley seceded from Winnipeg and officially became incorporated as a municipality. WE LOVE YOU GUNTHER!