| 1819 | January 29 | Sir Thomas Stamford Raffles an agent of the British East India Company arrives in Singapore looking for a suitable trading port. |
| January 30 | Sir Thomas Stamford Raffles signs a treaty with the Temenggong, the local chief, and Sultan Hussein of Johore-Riau to establish the Port of Singapore as, “a Free Port”. Raffles declares, “the trade thereof is open to Ships and Vessels of every Nation free of duty equally and alike to all.". |
| 1822 | | Sir Thomas Stamford Raffles designs a town plan for the new settlement of Singapore. |
| 1824 | March | The Netherlands recognizes British sovereignty over the Straits Settlements of Malacca, Penang and Singapore in return for British recognition of Dutch sovereignty in Bencoolen and the East Indies. |
| August 3 | A Treaty of Friendship and Alliance is signed with the Temenggong and Sultan Hussein placing Singapore under British governance. |
| 1823 | | Sir Thomas Stamford Raffles founds the Singapore Institution, the first secondary school for boys on the island. |
| 1826 | | The Straits Settlements; Malacca, Penang and Singapore, are placed under the administration of the British East India Company. |
| 1832 | | Admiral Sir Henry Keppel arrives in Singapore and begins clearing the Straits of pirates. |
| 1836 | March 26 | The Apostolic Church of Saint Gregory the Illuminator is opened to serve Singapore’s small but prosperous Armenian Orthodox community. The members include Catchick Moses, co-founder of The Straits Times, and the Sarkies Brothers, proprietors of the Raffles Hotel. |
| 1837 | | The first recorded game of cricket in Singapore takes place on a spot near the Padang. |
| | Saint Andrew’s Anglican Church, designed by G. D. Coleman of the Madras army, is completed. |
| 1840 | | The British Admiralty publishes the first navigation charts of Singapore waters. |
| 1845 | July 15 | The first issue of The Straits Times & Singapore Journal of Commerce is published by Robert Carr Woods. |
| During the Year | The Peninsular and Oriental Steam Navigation Company (P & 0) inaugurates its first scheduled steamship service through Singapore. |
| 1846 | | The Cathedral of the Good Shepherd, designed by Denis Leslie Mc Swiney and Singapore’s first Roman Catholic Church, is completed. |
| 1852 | | New Harbour, later known as Keppel Harbour, is surveyed and a deep water port is built. |
| | The Singapore Cricket Club is founded. |
| 1857 | | The Hotel de L’Europe opens. |
| 1858 | | The Government of India replaces the British East India Company as administrator of the Straits Settlements of Malacca, Penang and Singapore. |
| 1864 | | Saint Andrew’s Cathedral, designed by Colonel Ronald Macpherson of the Madras army, is complete after 8 years of construction employing Indian convict labor. |
| 1867 | April 1 | The Straits Settlements of Malacca, Penang and Singapore are declared a crown colony under the direct rule of the British Government. |
| July | Lady Ord, wife of Governor Sir Harry Saint George Ord, lays the cornerstone for Government House on a 100 acre plot of land purchased from Charles Prinsep's nutmeg plantation. |
| 1871 | | A submarine cable links Singapore with Madras permitting telegraphic communication with Europe. |
| 1877 | | The Chinese Protectorate, is established as an administrative body responsible for the well-being of ethnic Chinese residents of the Straits Settlements. In particular, it seeks to curb the human rights abuses of the coolie trade. |
| 1887 | September | A short article in the local press announces the intention of the Sarkies Brothers, proprietors of the Eastern & Oriental in Penang, to open a hotel in Singapore and name it after Singapore's founder Sir Stamford Raffles. |
| December 1 | The 10 room Raffles Hotel opens to the public at the corner of Beach and Bras Basah Roads on a site formerly occupied by the bungalow of Arab trader, Mohamed Alsagoff. |
| 1888 | | Henry Ridley is appointed director of the Singapore Botanic Gardens. Ridley goes on to develop the basic method for tapping the rubber tree: the removal at each tapping of a thin layer of bark from the cut end, thus permitting a smooth flow of latex and allowing the bark to regenerate. |
| | Author Joseph Conrad, then a seaman plying the eastern seas, is believed to be one of Raffles Hotel's earliest guests. Not long after, Rudyard Kipling who was on a round the world trip dined at the Hotel and writes, "Feed at Raffles". |
| 1889 | | The Chinese community presents a statue of Queen Victoria to the Governor, Sir Cecil Smith in the Jubilee Year of Her Majesty's rule as a memento of their loyal affections and gratitude for the benefit of her rule. |
| 1892 | August 29 | The Singapore Amateur Football Association is founded. |
| 1894 | December | The Palm Court wing of the Raffles Hotel opens. |
| 1899 | November 18 | The neo-Renaissance Main Building of the Raffles Hotel is opened. The new hotel boasts Singapore's first electric lights and fans and a French chef. |
| During the Year | The Tanjong Pagar Dock Company having gradually swallowed up its smaller rivals gains a virtual monopoly over the shipping business in Singapore. |
| 1902 | August | The last tiger to be killed in Singapore is shot while cowering under the Bar & Billiard Room of the Raffles Hotel. |
| 1904 | | The Bras Basah wing of the Raffles Hotel opens. The local press declares the Raffles, "the most magnificent establishment of its kind East of Suez”. |
| November 15 | Keppel Golf Club is founded. The Club's golf course is a 3-hole course built in the midst of a nutmeg plantation. |
| 1905 | | The Tanjong Pagar Dock Company is expropriated by the Government of the Straits Settlements. |
| 1907 | | The Hotel de L’Europe, rebuilt in Edwardian Baroque style, becomes a keen rival to the Raffles Hotel. |
| 1909 | | The Victoria Theatre is completed with addition of 54 meter clock tower linking the 1862 Town Hall and the 1905 Victoria Memorial Hall. |
| | The first British Military Hospital in Singapore is built on Sentosa Island. |
| | Electric lights and fans are installed in the Armenian Church of Saint Gregory the Illuminator. |
| ca. 1910 | Ngiam Tong Boon, a bartender at the Raffles Hotel, creates the Million Dollar Cocktail and Singapore Sling. |
| 1912 | | The Straits Settlement Port Ordinance establishes the Singapore Harbour Board. |
| 1915 | February 15 | The Indian 5th Light Infantry mutinies after hearing rumors that they are about to be sent to the front as cannon fodder. A European man runs on to the field half way through a cricket game on the Padang to tell the players that a mob of mutinous Indian soldiers are killing every European they can lay their hands on. The game is promptly abandoned as players disperse to various hiding spots. |
| 1919 | February 6 | Singapore’s centennial is marked by the transfer of the statue of Sir Thomas Stamford Raffles from its original site at the Padang to the space in front of the Victoria Memorial Hall. |
| 1921 | | Somerset Maugham makes his first visit to the Raffles Hotel. Legend has it that he worked all mornings under a frangipani tree in the Palm Court, turning the bits of gossip and scandal overheard at dinner parties into his famous stories. |
| October 1 | Singapore wins the first Malaya Cup (football) final with a 2-1 win over Selangor in Kuala Lumpur. Both teams field a goodly number of Europeans. |
| 1922 | March 31 | Singapore’s memorial to the dead of World War I is officially unveiled by the Prince of Wales when he stops in Singapore during a tour of India, Malaya, Australia and New Zealand. |
| 1923 | | The British Committee of Imperial Defence chooses a site at Changi just east of the causeway connecting Singapore and Malaya for construction of suitable facilities for the maintenance of a large battle fleet. An RAF Station is to be established at nearby Seletar to provide air defense. |
| 1927 | February | A three member commission headed by Major General Sir Webb Gillman arrives in Singapore to decide on the location of coastal batteries, types and calibers of the guns. |
| June | The Australian cricket tour of Singapore and Malaya brings life in the city to a halt. The Straits Times suggests that a two day public holiday be declared for the match. |
| 1930 | | The British Government halts construction of the Changi naval base. |
| | British playwright, novelist and actor Noel Coward appears as Captain Stanhope in the play Journey’s End at the Victoria Theatre. |
| 1931 | | The Great Depression and slump in the Malayan rubber trade take their toll on Singapore’s economy. The proprietors of the Raffles Hotel are forced into bankruptcy. |
| 1933 | | A Crowd of 10,000 packs the Anson Road Stadium to watch Singapore score the biggest Malaya Cup final win ever with an 8-2 thrashing of Selangor. |
| | The British Government resumes construction of the Changi naval base. |
| 1934 | | The bankrupt Hotel de L’Europe is torn down to make way for the Supreme Court building. |
| 1936 | June 1 | Singapore’s first radio broadcasting station goes on the air. |
| 1939 | August 3 | Sir Shenton Thomas, Governor of the Straits Settlements, presides at the opening of the Supreme Court building. |
| During the Year | The Cathay Building is opened by Dato Loke Wan Tho. It houses the headquarters of the British Malaya Broadcasting Corporation and Singapore’s first air conditioned theatre. |
| 1940 | | The Royal Army Medical Corps occupies the new Alexandra Hospital. |
| 1941 | | Ford Motor Company Malaya Limited opens the first automobile assembly plant in Southeast Asia in a new art deco factory at Bukit Timah. |
| December 8 | Japanese troops invade Malaya. As the Japanese push their way south, the stream of people and equipment into Singapore turns into a flood. The battleship HMS Prince of Wales and the battle cruiser HMS Repulse steam out of Singapore to intercept Japanese forces landing further up the coast of Malaya. |
| December 9 | The Japanese attack Royal Air Force landing fields in Singapore destroying nearly all of the British airplanes. |
| December 10 | Japanese torpedo bombers sink HMS Prince of Wales and HMS Repulse in the Straits of Malaya. |
| December 11 – 12 | A 65,000 man Japanese army under General Tomoyuki Yamashita defeats the 90,000 man British, Indian and Australian force commanded by Lieutenant General Arthur Percival at Jitra, Malaya opening the path to Singapore. |
| December 16 | British civilians and government officers in Penang flee for the safety of Singapore abandoning the natives to their fate. |
| 1942 | January 31 | British and Australian forces withdraw from Malaya to Singapore blowing a fifty meter gap in the causeway behind them. |
| February 8 | At least 50 boats laden with members of the 5th and 18th Japanese army divisions cross the Johore Straits separating Singapore from the Malay Peninsula during the night. |
| February 11 | Japanese forces take Bukit Timah Hill, the highest point on Singapore Island, despite fierce resistance from British troops and Singapore Chinese irregulars. The British fall back to a line stretching from Pasir Panjang to Kallang. General Yamashita calls on the British to surrender. |
| | Brigadier C.H. Stringer, commander of the medical services for the Malaya Force, recommends to Lieutenant General Percival that from a medical standpoint it would be wise to capitulate immediately before the outbreak of malaria and hygiene related diseases becomes uncontrollable. |
| February 12 | The last broadsheet edition of The Straits Times is printed before the Japanese advance reaches the heart of Singapore. |
| February 13 | The Straits Times is reduced to a small single-sided sheet, distributed free by members of staff or left at air-raid precautions stations. |
| | General Percival cables General Wavell for permission to surrender, hoping to avoid the destruction and carnage that would result from a house to house defense of the city. |
| February 14 | 1 p.m. - The Japanese capture most of Singapore. Japanese troops massacre more than 200 patients and staff at the Alexandra Military Hospital. |
| February 15 | The last issue of The Sunday Times before the Japanese Occupation is published. |
| | British colonists gather at the Raffles Hotel to dance and sing “There Will Always Be An England”. |
| | 6:10 p.m. - Lieutenant-General Arthur Percival surrenders to Lieutenant General Yamashita Tomoyuki in the Ford Motor plant at the foot of Bukit Timah Hill. Under the terms of the surrender, 1,000 Japanese troops are sent into the city to maintain order until the Japanese Army complete their occupation. |
| February 17 | Singapore is renamed Shonan, "Light of the South", by the Japanese. |
| February 21 | The Japanese carry out Operation Sook Ching. Chinese Males between the age 18 to 50 are required to report to Sook Ching centres to be screened. Between 25,000 and 50,000, those considered an "undesirable" threat to the Japanese are executed. |
| February | The main military prison camp is established in the Singapore jail, about 9 miles outside the town. Up to 11,000 Prisoners of War, British, Australians and Dutch are held during he war. |
| March | Shigeo Odate is appointed Mayor of Shonan. |
| During the Year | The Raffles Hotel is renamed Shonan Ryokan (Light of the South Hotel) by the Japanese occupiers. The Raffles Library and Museum manages to stay intact under the charge of Japanese vulcanologist Professor Hidezo Tanadate, who is on friendly terms with General Yamashita, the Commander of the conquering Japanese Army. |
| 1943 | July 19 | Kanichi Naito is appointed Mayor of Shonan. |
| 1945 | September 5 | The British return to Singapore following the Japanese surrender. |
| | The Raffles Hotel becomes a temporary transit camp for war prisoners released under the military administration. |
| September 7 | The first postwar issue of The Straits Times is published. |
| September 12 | Supreme Allied Commander Admiral Lord Louis Mountbatten accepts the formal unconditional surrender of 680,000 Japanese soldiers in South East Asia by General Itagaki Seishiro in the Council Chambers at the Municipal Buildings in Singapore. |
| | The original Union Jack which the Japanese had ordered carried through the streets of Singapore with a white flag when the British surrendered in 1942 is hoisted on the flagstaff in the centre of the parade ground in front of the Municipal Buildings. |
| 1946 | April 1 | The British Military Administration is dissolved. Singapore is made a crown colony separate from the Straits Settlements. |
| 1947 | June 26 | Seven Japanese officers including Lieutenant Generals Takuma Nishimura and Saburo Kawamura are executed for war crimes arising from their participation in Operation Sook Ching, the systematic extermination of Singaporean Chinese. |
