The original leaf drawn by Alan Beddoe had 13 points. When a sugar maple leaf model was tested in the wind tunnel of the National Research Council's laboratory, the 11-pointed model appeared more aesthetic and elegant. Jacques Saint-Cyr, a graphic artist working for the Canadian Government Exhibition Commission, stylized the 11-point maple leaf that was presented to the Canadian Parliament.

The first recorded flag to fly on Canadian soil was the Cross of St. George. In 1497, Italian seafarer John Cabot explored and claimed Canada's Atlantic coast in the name of King Henry VII of England. The Cross of St. George was carried by John Cabot when he reached the east coast of Canada in 1497. A watercolour painting by John White depicted English explorers with the Cross of St. George during Martin Frobisher’s expedition of 1577.

In 1534, French explorer Jacques Cartier explored the Gulf of Saint Lawrence where, on July 24, he planted a 33 ft cross bearing the words "Long Live the King of France" and took possession of the territory 'New France' in the name of King Francis I. The fleur-de-lis was a symbol of French sovereignty in Canada from 1534 to 1763. In 1763, as a result of the French and Indian Wars, France lost its colonial possessions in Canada ceded the territory to the United Kingdom.

At the time of Confederation, Canada's national flag remained the Union Jack. However, Sir John A. Macdonald, Canada's first Prime Minister, flew the Canadian Red Ensign as a distinctive flag of Canada. It was never officially adopted by the Parliament of Canada. It featured the Union Flag in the canton, defaced with the shield of the Coat of Arms of Canada.

A new Canadian Red Ensign was adopted in 1921 that is a red field, featuring the British flag in the canton, defaced with the shield of the Coat of Arms of Canada. The shield contained the three golden lions, the red lion rampant of Scotland, the Irish harp of Tara, the gold fleurs-de-lis of royal France and a sprig of red maple leaves at the bottom.

A new Canadian Red Ensign was adopted in 1957 that is a red field, featuring the British flag in the canton, defaced with the shield of the Coat of Arms of Canada. The Green Maple leaves from the previous flag were changed to red maple leaves

In 1964, Prime Minister Lester B. Pearson made the creation of a new Canadian flag a priority. After eliminating thousands of proposals, the Special Committee on a Canadian Flag was left with three possible designs: one incorporating three red maple leaves with blue bars (nicknamed the "Pearson Pennant"), a flag with a single stylized red maple leaf on a white square with red bars, and another version that contained both the Union Jack and three fleurs-de-lis. On January 28, 1965, the National Flag of Canada was proclaimed by Her Majesty Queen Elizabeth II, to take effect on February 15, 1965. The inspiration for a red and white flag came from Dr. George Stanley, Dean of Arts at the Royal Military College in Kingston, Ontario. Impressed by the Commandant's flag at the College (a mailed fist holding three maple leaves on a red and white ground), Dr. Stanley suggested to Mr. John Matheson a similar design with a single red maple leaf at the centre. This red - white - red pattern bore a strong sense of Canadian history: the combination had been used as early as 1899 on the General Service Medal issued by Queen Victoria.

The current Canadian flag was inaugurated on February 15, 1965 at an official ceremony held on Parliament Hill in Ottawa. National Flag of Canada Day, instituted in 1996, is observed annually on February 15 to commemorate the day the flag was unfurled on Parliament Hill. It is not a public holiday.

No law dictates the proper use of the Canadian flag.
However, Canadian Heritage has released guidelines on how to correctly display the flag alone and with other flags. The guidelines deal with the order of precedence in which the Canadian flag is placed, where the flag can be used, how it is used, and what people should do to honour the flag. The suggestions, titled Flag Etiquette in Canada, were published by Canadian Heritage.
The flag itself can be displayed on any day at buildings operated by the Government of Canada, airports, military bases, and diplomatic offices, as well as by citizens, during any time of the day.
When flying the flag, it must be flown using its own pole and must not be inferior to other flags, save for, in descending order, the Queen's standard, the governor general's standard, any of the personal standards of members of the Canadian Royal Family, or flags of the lieutenant governors.
The Canadian flag is flown at half-mast in Canada to indicate a period of mourning.
When the Canadian flag flies along with the flags of the 10 provinces and 3 territories, the flags of the provinces and territories follow in the order that they entered Confederation. For those years when multiple provinces entered Confederation, their flags are arranged by size of the population at the time of entry. The order of precedence is therefore as follows: Ontario (1867), Quebec (1867), Nova Scotia (1867), New Brunswick (1867), Manitoba (1870), British Columbia (1871), Prince Edward Island (1873), Saskatchewan (1905), Alberta (1905), Newfoundland and Labrador (1949), Northwest Territories (1870), Yukon (1898) and Nunavut (1999)

The Royal Standard of Canada is a heraldic banner adopted and proclaimed by Queen Elizabeth II in 1962 for her use in her capacity as Queen of Canada.
The flag, in a 1:2 proportion, consists of the escutcheon of the Royal Coat of Arms of Canada in banner form defaced with the distinct device of Queen Elizabeth II used on her Head of the Commonwealth flag: a blue roundel with the initial E surmounted by St Edward's Crown and within a wreath of roses, all gold-coloured.

The current flag of the Governor General of Canada, adopted in 1981, comprises the crest of the royal coat of arms of Canada—a crowned lion holding a red maple leaf in its paw, standing on a wreath of red and white on a blue background.