Archaeological evidence of a Norse settlement was found in L'Anse aux Meadows on Newfoundland. It is very unlikely that the Viking explorers used any flags at all. Since the Vikings left few writing records of their explorations except those found in the famous Norse Sagas where no flags were mentioned. However, the Raven Banner (Guðfani) is the most commonly reported Norse "flag" and it is possible that it might have been brought to Newfoundland. We do know that Viking explorers like Bjarni Herjulfesson, Helge Ingstad, Eric the Red, and Leif Ericsson all played a part in the early exploration of Newfoundland between AD 800-1000, but again there is no historical documentation to support the assumption that Raven Banner or any other flag was used.

There is a fantastical account of an Irish monk named Saint Brendan the Navigator who made a sea voyage in the early 6th century to Newfoundland from Ireland. While the story itself is a part of Irish myth and legend, some historians believe it is based on fact.

Portuguese explorers were active in Canadian waters throughout 1600s. In 1501 and 1502, Portuguese brothers Miguel and Gaspar Corte-Real explored Newfoundland and Labrador, claiming them as part of the Portuguese Empire.

Newfoundland has always been called "England's oldest colony" in Canada based on the arrival of John Cabot in 1497 and Sir Humphrey Gilbert's claim in 1583, but from the very beginning, France was also an important participant in the exploration and exploitation of Newfoundland. Although the French explorer Jacques Cartier arrived in 1534, Breton, Norman and Basque fishermen had already been fishing in Newfoundland's waters for over thirty years.

The Newfoundland Natives' Society (NNS), a non-denominational organization founded in 1840 "to protect the rights and privileges of Newfoundland-born citizens against the flood of newcomers to the island in the mid-nineteenth century", provided Newfoundland with one of its earliest versions of a "native" tricolor flag. The NNS's first silk flag (not shown) is clearly documented. It had a elaborate shield centered on it depicting aspects of Newfoundland life. There were clasped hands above the shield and the words "Union and Philanthropy" below it. The whole flag had a red background.

Although the usual flag to fly on the Government House in St. John's would probably have been the Union Jack, this flag was shown on the Government House in a book of water-colors made in 1862 called The "Corrected Code of Merchant's Signals". It was most likely a "Governor's Flag" used in the 1860s before the introduction of the defaced Union Jacks in 1870.

Another variant of the Governor's Flag appearing around 1870 was basically a blue British ensign defaced with a simple white circular shield with the words "Terra Nova" (new land) written in red beneath a royal crown. The only official reference found to these pre-1870 governor's flags was in the 1862 edition of "Queen's Regulations & Admiralty Instructions". It was found in the section dealing with Ceremonial and Distinctions and was included with a Colonial Office Circular of 17 Oct 1862. V-4.

The flag commonly presented as the Newfoundland Tricolor, or the "Green, White and Pink", is a traditional flag very popular in the Newfoundland and Labrador area, but has never been "officially" recognized in any way by the government. Popular tradition claims it was originated in the 1880s or 1890s as the flag of a Roman Catholic fraternal group named "The Star of the Sea Association" (founded 1871) in St. John's. It is one of the few recognized flags in the world to use the color pink (occasionally called rose) in its design. Many times, although normally displayed in a "Green, White, & Pink" pattern, it also is mirrored or reversed into a "Pink, White, & Green": pattern.

The Red Ensign was officially endorsed by King Charles II in 1674; this authorization recognized it as the ensign of English merchant shipping. Later, during the Victorian era, the flag with colonial badge formed the basis as the Colony of Newfoundland's civil ensign.

From 1931 until confederation with Canada in 1949 the Union Jack was legislated as the national flag of Newfoundland. Then from 1952 until 1980 the Union Jack was readopted as the official flag of the province of Newfoundland. Ottawa's refusal to recognize the Union Jack as a unique representation of the province led to the provincial government seeking a new Newfoundland flag and the eventual design and adoption of Christopher Pratt's deconstructed Union Jack-based design as the Flag of Newfoundland and Labrador on May 28, 1980.

The flag of the Fédération des Francophones de Terre-Neuve et du Labrador is based on the French tricolor and Acadian flag, with three unequal panels of blue, white, and red. Two yellow sails are set on the line between the white and red panels. The sail on top is charged with a spruce twig, while the bottom sail is charged with a pitcher flower. These emblems are outlined in black.

The Labrador Flag was created by the Member of the House of Assembly for Labrador South, Mike Martin in 1974. Martin did so as an affront of political mischief aimed at Joey Smallwood and his indifference to Labrador. As Martin is from Cartwright, the town now proclaims itself the "Birthplace of the Labrador Flag".

The flag was presented to Labrador community councils, and to the Labrador members of the House of Assembly, in April 1974.

Labrador's name in the Inuttitut language (spoken in Nunatsiavut) is Nunatsuak, meaning "the big land" (a common English nickname for Labrador). Newfoundland's Inuttitut name is Ikkarumikluak meaning "place of many shoals".

As a former colony and then dominion of the United Kingdom, Newfoundland gave up its independence in 1933. It became the tenth province to enter the Canadian Confederation on March 31, 1949, as "Newfoundland." On December 6, 2001, an amendment was made to the Constitution of Canada to change the province's official name to "Newfoundland and Labrador."