The unincorporated community of Headingley is situated within the municipality along Manitoba Provincial Road 334 near the Trans-Canada Highway.

The municipality takes its name from the suburb of Headingley in the city of Leeds in West Yorkshire, England.

[5] The first permanent European residents of the present-day Headingley area are figured to have been Oliver Gowler (1814–1865) and his wife, Mary (Nee Lady Neville Braybrooke) (1816–1878), who came to Canada together in the fall of 1836, hired by the Hudson ’s Bay Company to work on their experimental farm at Red River.

In the late 1860s, Reverend George Young, the first Methodist missionary in Red River, began to visit Headingley regularly.

[6]In the early part of the 20th century, an interurban train, Route 29, operated by the Suburban Rapid Transit Company, Manitoba served the Headingley area; however, this line was discontinued in the 1930s.

Initial discussions about Headingley seceding from Winnipeg began in March 1987 over concerns about municipal tax rates.

Headingley residents wanted the City and Province to spend $4 million on extending water services to the community.

[6] In 2013, the Manitoba government decided to divide a 1.7-kilometre (1.1 mi) section of the Trans-Canada Highway that runs through Headingley, because it was notorious for vehicle accidents.

Headingley is also a member of the Boyne River Mutual Aid Fire District, which provides backup and support services on an as-required basis.

[22] Local businesses located in Headingley include T&T Seeds, Shelmerdine's Nurseries, Flying J, The Gates on Roblin, and Taillieu Construction.