| DATE | BRIEF DESCRIPTION |
| 1874 | Born November 30, eldest son of Lord Randolph Churchill and American heiress Jennie Jerome. |
| 1898 | Cavalry officer in India and Sudan. |
| 1899 | War correspondent in South Africa - imprisoned by the Boers, but escapes. |
| 1900 | Elected Conservative MP for Oldham. |
| 1904 | Changes political allegiance to the Liberal Party over free trade issue. |
| 1908 | President of the Board of Trade in Asquith's government. |
| 1910-1911 | Home Secretary. |
| 1911-1915 | First Lord of the Admiralty. Failure of naval campaigns leads to demotion. |
| 1917 | Minister of Munitions in Lloyd George's government. |
| 1919-1921 | Secretary for War and Air. |
| 1921-1922 | Colonial Secretary. |
| 1922 | Collapse of Lloyd George's government |
| 1924 | Elected Conservative MP for Epping. |
| 1926 | Chancellor of the Exchequer during the General Strike, which he vigorously condemns. |
| 1929 | Fall of Baldwin's government. Beginning of period in political wilderness, speaking out against prevailing policies of disarmament and appeasement with Nazi Germany. |
| 1939 | War cabinet post as First Lord of the Admiralty. |
| 1940 | Becomes Prime Minister on Chamberlain's resignation. Speeches rally the nation after the fall of France and the evacuation of Dunkirk. |
| 1941 | Soviet Union and the United States join the Allied cause against Axis powers. |
| 1945 | Yalta Conference fixes post-war political map of Europe. Defeated by Labour Party landslide in General Election. |
| 1946 | Makes Iron Curtain speech warning of Soviet threat and division of Europe. |
| 1951-1955 | Prime Minister, but efforts handicapped by old age and poor health, which eventually leads to his resignation. |
| 1965 | Dies January 24 in London. |
