The hill has a long history intertwined with that of the country due to its location as the highest elevation within walking distance to the city's civic district, within the Downtown Core.

A settlement on the hill in the 14th century was referred to as Ban Zu (from the Malay pancur) by the Yuan dynasty traveller Wang Dayuan.

It is believed that the Fort Canning Hill area was once the centre of ancient Singapura that thrived in the 14th century, and was occupied by a palace with various buildings of political, religious and commercial significance.

[5][6][7] A series of archaeological digs that began in 1984 have uncovered evidence of workshops for glass and gold that dated to the 14th century, and a ceremonial or religious area near the summit.

[8] Historical sources also indicate that around the end of the 14th century, Singapura was attacked by either the Majapahit or the Siamese, forcing its ruler Parameswara to move on to Melaka where he founded the Sultanate of Malacca.

In the early period of 19th century Singapore, the stream was used to provide clean drinking water for all ships stopping at the port until the demand exceeded the capacity, and the spring dried up as wells were dug around the hill.

[13] On 6 February 1819, Temenggong Abdul Rahman and Sultan Hussein Shah signed The Singapore Treaty with Stamford Raffles.

Farquhar drew up the first gun and set up the post to hoist the Union Jack on top of the hill, marking the birth of Singapore as a British settlement.

Upon his return in October 1822 and impressed with Coleman's design, Raffles approved the house, construction of which was soon begun on Singapore Hill in November 1822 and completed by January 1823.

[16] On 2 August 1824, Temenggong Abdul Rahman, Sultan Hussein, and John Crawfurd signed the Treaty of Friendship and Alliance at the hill.

[19] A report recommended extensive fortifications, which alarmed the business community who felt a large fortress would be detrimental to trade.

[19] However, the fortifications were considered a failure from the beginning, as ships could easily get close enough to destroy the town yet remain out of range of the fort's guns.

[15] Under the British Army, it served as the headquarters of the Singapore Base District until the spread of World War II into the Asia Pacific in 1941.

The Van Kleef Aquarium was first constructed in 1955 at the foot of Fort Canning Hill known as King George V Jubilee Park facing River Valley Road.

The unique blend of historical relics, lush greenery and expansive lawns has made Fort Canning a hub of cultural and artistic activity.

It has been a venue of choice for staging myriad outdoor events and activities like theatre carnivals such as Shakespeare in the Park by SRT, art festivals, starlight cinemas and Ballet Under the Stars performances.

[29] Fort Canning Park has been designated as the venue of the bicentennial showcase in 2019, an event which commemorates 200 years since the founding of Singapore.

Other enhancements to the park include a new heritage museum at the Fort Canning Centre, a reproduction of an ancient spring and improvements in accessibility.