In the 1980s, Sobeys expanded into southern Ontario, challenging Loblaws on its "home turf", thereby igniting what came to be a nationwide battle for market supremacy.

In 1998, Sobeys became the second-largest grocer in the country after purchasing the Oshawa Group, owners of the IGA franchise across Canada, along with several regional chains in Ontario, in addition to various food service and wholesale companies.

In 2002, Sobeys undertook major changes in its store design and customer service policies with the introduction of "Ready to serve".

This initiative was reportedly an attempt to emulate the successful moves of the Publix supermarket chain in the southern United States.

[8] In 2005, Sobeys lost a bidding war with Quebec-based Metro to acquire A&P Canada, operator of several Ontario supermarket chains.

It is also suggested that the Sobey family was unwilling to cede any control to the Tengelmann Group, the ultimate parent company of A&P at the time.

[11] In September 2011, Sobeys' wholesale division signed a long-term distribution agreement with American retailer Target for the supply of select food and grocery products to its Canadian stores.

[13] In June 2013, Sobeys announced the purchase of Safeway's Canadian operations for $5.8 billion, subject to regulatory approval.

[14] As a condition of the deal imposed by the Competition Bureau in October 2013, Sobeys was required to sell 23 of its retail locations to other companies.

The Financial Post also reported that changes made by Sobeys, including the discontinuation of its popular loyalty program, the replacement of Safeway's house brands with Sobeys' brands, reports of poorly stocked inventories at Safeway locations, had impacted the chain's customer loyalty.

[22] In January 2018, Sobeys announced an agreement with Ocado to open an e-commerce grocery fulfilment centre in Toronto during late 2020.

[24] In late January 2018, Sobeys announced that it would, in the wake of the Safeway purchase, close an additional 10 of its "underperforming" locations.

[11] At the time of the Sobeys takeover of the Oshawa Group, all IGA locations in Atlantic Canada were purchased separately by Loblaws for competition reasons.

[14] Sobeys operates the smaller grocery store Foodland chain, mainly in rural areas of Newfoundland and Labrador, Nova Scotia, New Brunswick and Ontario.

In April 2019,[35] FreshCo launched in Western Canada, opening three stores in British Columbia and two in Winnipeg, as well as two Chalo!

The company delivers products to retail outlets, such as convenience stores and gas stations, throughout Atlantic Canada.

[39] On September 24, 2018, Empire Co. Ltd., Sobeys' parent, announced it had signed an agreement to purchase Farm Boy, an Ontario chain of 26 supermarkets, for $800-million.

Farm Boy founder Jean-Louis Bellemare and his co-CEO Jeff York will continue in their roles, since the company will operate as a separate entity.

The move allows Farm Boy to continue with aggressive expansion plans into Southwestern Ontario, particularly the Toronto region.

[41] As of mid-August 2022[update], in Quebec, Ontario and western Canada, Sobeys and its affiliated banners continue to offer the Air Miles loyalty rewards program.

At various times prior to joining Air Miles, Sobeys-owned locations in many regions offered the in-house Club Sobeys/Club Thrifty Foods program.

[43] In June 2022, Empire Company announced that it will end its participation in Air Miles and switch to the Cineplex Entertainment and Scotiabank-owned Scene+ program at its grocery and pharmacy chains.

A Bloomberg News reporter who viewed a video of a similar system described the process: "[The] similar Ocado facility in Andover, England, shows the facility spanning nearly 21,000 square metres (5¼ acres) with robots rolling over a grid to pick and pack customer orders in about five minutes."

[55] Its stores are located across Canada with 54 in Alberta, 1 in British Columbia, 17 in Manitoba, 23 in New Brunswick, 14 in Newfoundland and Labrador, 42 in Nova Scotia, 90 in Ontario, 5 in Prince Edward Island, and 10 in Saskatchewan.

The Empire Company also owns the trademarks to their former Empire Theatres cinema chain, which was until October 2013 Canada's second-largest movie theatre chain, when its locations were split between Cineplex Entertainment (Atlantic locations) and Landmark Cinemas (Ontario, British Columbia, and Alberta).