Winn-Dixie is known for its private label Chek brand soft drinks, which are produced in over 20 different flavors plus diet and caffeine-free varieties—one of the widest assortments.

[4] In its advertising and print media, Winn-Dixie used slogans such as “We’re Right For You” starting in 1982, “America’s Supermarket” from 1985 until 2001, “The Real Deal” from 2001 to 2004, and since 2018, “It’s a Winn Win!” Winn-Dixie has also been known for its use of the brand promises of "Fresh Checked Every Day" for its Jacksonville, Florida locations, "Getting Better All The Time" in its locations in Central Florida, "El Sabor De Tu País", or "The Flavor Of Your Country", in its Miami area stores, and "Local Flavor Since 1956" in its Louisiana area stores.

Winn-Dixie was listed in the S&P 500 and had been traded on the New York Stock Exchange under the ticker symbol "WIN" since February 18, 1952,[4] prior to filing for Chapter 11 bankruptcy in 2005.

[4][9] In 1952, Winn & Lovett became the first industrial corporation based in Florida to be listed on the New York Stock Exchange (NYSE).

[9] In 1967, Winn-Dixie bought the City Markets chain in the Bahamas, effectively extending their reach into the Caribbean.

[12] Operating 12 stores through its domestic subsidiary, W-D (Bahamas) Limited, until it sold the chain to Bahamian investors in 2006.

By this time, it had set up division offices and distribution centers in Charlotte, Orlando and Fort Worth.

[21][22][23] Winn-Dixie underwent a major restructuring, announcing in April 2000 that it was cutting 11,000 jobs and closing 114 stores.

It faced significant competition from Wal-Mart, with many stores overlapping, and needed to make major investments in order to modernize.

[27][28] In May 2002, Winn-Dixie announced it was closing all its stores in Texas and Oklahoma, and laying off 5,300 employees, citing increased competition from Wal-Mart.

By July, Winn-Dixie agreed to sell several Thriftway locations to Kroger, Remke Markets, and Bigg's Supermarkets.

On February 28, 2006, it was announced that 35 more stores were to be sold or closed within the coming months, with the Central and South Florida areas being the most affected.

[39] On March 31, 2006, it was announced that the chain would sell its 12 Bahamian locations, which had been operated by a wholly owned subsidiary, W-D Limited, under the names City Market and Winn-Dixie.

[40][41] On June 29, 2006, Winn-Dixie announced that it had filed a plan of reorganization with the U.S. Bankruptcy Court for the Middle District of Florida.

[46] The merger was completed in March 2012, making Winn-Dixie a subsidiary of Bi-Lo Holdings, ending 67 years of Davis family ownership.

The combined company operates 750 stores in seven southeastern states, employing approximately 63,000 team members.

[50][51][52] In July 2017, it was announced that Southeastern Grocers would debut the Harveys brand in the Central and West Florida markets with the conversion of seven Winn-Dixie stores.

[57][58] On March 22, 2018, it was announced that the Orange Beach, Alabama Winn-Dixie location was being sold to Rouses Markets.

[59] On March 28, Southeastern agreed to sell three Winn-Dixie stores in northeast Alabama to wholesaler Mitchell Grocery Corp on behalf of two of its current customers, Johnson's Giant Foods and The D'Alessandro Organization LLC, while the Winn-Dixie location in Atmore, Alabama, was being acquired by Ramey's.

[60][61] On March 31, 2018, it was announced that the Andalusia, Alabama Winn-Dixie location's lease and equipment would be purchased by a Piggly Wiggly franchisee.

[62] On May 1, an independent Piggly Wiggly operator announced that they would re-open the Montgomery, Alabama Winn-Dixie location that closed as part of the original restructuring plan.

[66] In 2020 Southeast Grocers began the Romay Davis Belonging, Inclusion and Diversity Grant with the goal of funding minority-supporting organizations.

[6] Stores will either remain open under the Winn Dixie or Harvey's brand or convert to the ALDI Süd format.

[72] Aldi’s will run its 220 acquired stores from the sale through its licensing with the company until the last location is converted to its format by 2027.

"[73] It is reported that after reading Booker T. Washington's Up From Slavery, James E. Davis began a program of Winn-Dixie supporting historically black colleges and universities.

Davis spearheaded a $6 million corporate fund-raising drive and donated 140 acres of property to the Mayo Clinic in order to build a new facility in Jacksonville.

[77] As of November 28, 2022, Winn-Dixie operates more than 546 grocery stores in Florida, Alabama, Louisiana, Georgia, and Mississippi.