Pick n Pay (officially Pick n Pay Group Ltd) is a major South African grocery retail chain, headquartered in Cape Town. It operates both corporate and franchised stores under two brands – Pick n Pay (which includes its Supermarket, Clothing, Liquor, Build, and Hypermarket stores), and Boxer.

Pick n Pay was founded by Raymond Ackerman, son of Gus Ackerman, who founded the Ackermans clothing retail chain in South Africa, in 1916. Raymond joined Ackermans in 1951 as a trainee manager. In the early 1950s, Ackermans was sold to rival department store chain Greatermans. When Greatermans branched into food retailing, Ackerman recognised the potential for a new type of shopping experience - self-service supermarkets. He encouraged Greatermans to start its own supermarket chain, of which Ackerman would become General Manager. The first store was opened in Mayfair, Johannesburg. The new chain, Checkers, still exists in South Africa, as a major competitor to Pick n Pay.

In 1966, after nine years of running Checkers and taking the number of stores from 4 to 85, Raymond purchased the first four Pick n Pay stores in Cape Town from Jack Goldin.

In 1975, Pick n Pay opened its first Hypermarket - a new retail concept which combined department store and supermarket operations under one roof.

Pick n Pay launched its first franchised store in 1993, in Westville, KwaZulu-Natal. Its first franchised store in the Western Cape was opened in Durbanville in 1994.

In 1997, the company held its first franchise conference, and in 2003, opened its first franchised Pick n Pay Clothing store.

In 2010, Raymond Ackerman resigned as Pick n Pay Chairman. His son, Gareth Ackerman, took over the position.

Pick n Pay acquired a majority stake in the Score supermarket group in 1994.