Fort Canning Hill was once known as Bukit Larangan (Forbidden Hill) and later as Government Hill when the British established Singapore as a crown colony. Malay and Chinese historical records indicate that this was the site of an ancient kingdom around 1300AD. Its name, Bukit Larangan stemmed from the belief that no one was permitted to go up the hill without being summoned by the ancient Malay rulers, whose royal palace probably stood on the summit.

Various archaeological digs at Fort Canning Park in 1984 reinforced the existence of this golden era of the five kings in 14th Century Singapore prior to the arrival of the British in 1819. Thousands of artefacts indicated a high likelihood of the area being used by palace craftsmen to manufacture glass and gold items. All these further lend evidence to the historical significance of Fort Canning.

Raffles built his residence, the Government House on the hill in 1823 during his third and last visit to Singapore. The site of his residence commandeered a magnificent view of the harbour and remained there till 1895 when construction began on Government hill to build a fort. Fort Canning was named after Viscount Charles John Canning, Governor-General and First Viceroy of India.

Prior to the opening of a cemetery at Bukit Timah Road, an old Christian cemetery existed here between 1830s and 1865. It was consecrated by Bishop Wilson of Calcutta in 1834. A Gothic-styled gateway to the cemetery still stands today and dates back to about 1833.

Fort Canning also has a military past. It was here in the underground operations rooms (the current Battle Box) that General Percival made the decision to surrender Singapore to the Japanese on 15th February 1942. The former military barracks have been converted to the Fort Canning Centre which today houses some of the arts groups like the Singapore Dance Theatre.