In 1952, Sears Chairman General Robert E. Wood sent a letter to Simpsons President Edgar G. Burton, proposing a partnership between their two companies in order to serve the Canadian market.

The company made its public debut on the Toronto and Montreal stock exchanges on April 5, 1965, with the listing of its Class “A” non-voting shares.

The following year Simpsons-Sears opened a store at Square One Shopping Centre in the city of Mississauga, approximately 30 km (19 mi) west of Toronto.

The Simpsons-Sears agreement had largely shut out Sears from the urban core, and that remained so even when the restriction was lifted, as The Bay and Eaton's long held a duopoly in the downtowns of major Canadian cities.

Sears Canada had also entertained notions of obtaining the former Eaton downtown Montreal store but that location was eventually occupied by Quebec retailer Les Ailes de la Mode.

Sears Canada announced it would end its credit card partnership with JPMorgan Chase when the agreement expired in November 2015.

A ruling by the Ontario Securities Commission, made in August 2006, stalled progress the attempted privatization by its parent company, Sears Holdings Limited.

[3][25] In December 2011, after slow sales over the holiday season, Sears laid off 70 employees from its head office after losing nearly $47 million in the previous quarter.

Among the planned changes were to build upon market segments where Sears had historically performed well (including appliances, dresses, children's wear and related products, and mattresses), and introduce a new store format with a more "engaging" layout.

[6] In April 2013, the company began to scale back some of its product offerings, dropping electronics and window coverings, and making toys online-only.

[34] The new format was designed to have a more open layout with fewer permanent displays and partitions, providing more flexibility in how departments are arranged and stocked.

The footwear department was also moved to the centre of the store and switched to a "self-serve" concept, with product boxes accessible by customers (thus reducing the need for dedicated associates).

Stranzl stated that the new format was meant to "take ideas from the best in the business, whether it's in shoes, outerwear or appliances", and return the chain to a "price-focused" strategy.

The company had also been reducing its product assortment to have a larger focus on fashion and home decor, downplaying its automotive, electronics, and tool businesses.

The company stated that its new strategies and positioning were "starting to resonate with consumers", citing increasing same-store sales over the previous two quarters.

The owners of five Alberta dealers reported that most of their locations were still profitable, and stated that due to the restructuring proceedings, they were losing compensation prescribed by their contracts with Sears if the retailer terminates them early.

A company representative stated that Sears Canada "shares everyone's concerns about the plight faced by some of its former employees, and is glad to see a solution, pending court approval, that can at least help those most in need."

"Following exhaustive efforts, no viable transaction for the company to continue as a going concern was received," Sears Canada announced on October 10, 2017.

[53] In an attempt to moderate the hardship for retirees, a judge had previously ordered payments to other Sears creditors frozen until the pension issue was resolved.

The concept was eventually expanded nationwide, offering consumers an off-priced selection of in-house and brand name products.

were designed to serve smaller-sized markets and bring a displayed selection of big ticket merchandise, along with the convenience of a local Catalogue counter, to consumers not near larger Sears stores nor other large retail firms.

This change was intended to reflect their broader appeal for customers seeking a one-stop experience for re-making their home decor.

In 2016, the company launched Initium, an initiative to overhaul existing legacy platforms into a new cohesive, functional, adaptable and user-friendly online retail enterprise for consumers.

[58] After October 19, 2017, the website was no longer available for online purchases and directed shoppers to the remaining stores undergoing liquidation, with a message of thanks to customers.

[60] As a part of the bankruptcy protection process, Corbeil was sold to Am-Cam Électroménagers Inc., headquartered in Montreal, for an undisclosed amount.

The headquarters moved there from 222 Jarvis Street after that building was sold in 2007 to the Ontario Realty Corporation and houses provincial government use since 2011.

Silvertone was the brand name used by Sears, Roebuck and Co. for its line of sound, radio, stereo and home entertainment equipment from 1915 to 1972 and by Simpsons-Sears in Canada from 1953 to 1972.

Jerry Garcia, Chet Atkins, Bob Dylan, John Fogerty, Jack White, Mark Knopfler, and Brad Paisley had a Silvertone for their first electric, bass, or acoustic guitar.

Jessica was Sears Canada's primary private label brand of women's apparel and accessories, catering to the modern woman.

[71] Indigo Books and Music acquired the Calgary Distribution Centre and Subsidiary SLH Transport was sold to Quebec-based C.A.T.