| 1874 | WSC born November 30 at Blenheim | |
| 1886 | His father becomes chancellor of the Exchequer | |
| His mother is now a great Victorian courtesan | ||
| 1888 | WSC enters Harrow; gets lowest marks in school | |
| 1893 | Admitted to Sandhurst on third try | |
| 1894 | Commissioned cavalry subaltern, Fourth Hussars | |
| 1895 | His father dies | |
| WSC covers the guerrilla warfare in Cuba | ||
| 1896 | Educates himself in India; discovers Macaulay and Gibbon | |
| Writes first book | ||
| 1897 | Sees heavy fighting in Khyber Pass | |
| 1898 | Omdurman: WSC in the last cavalry charge | |
| 1899 | WSC runs for Parliament; loses | |
| Captured in the Boer War | ||
| His sensational escape | ||
| 1900 | Recommended for VC | |
| Elected to Parliament | ||
| Tours United States, Canada | ||
| 1901 | Queen Victoria dies | |
| WSC’s maiden speech | ||
| 1904 | Quits Tories for Liberals | |
| 1905 | Becomes colonial under secretary | |
| 1907 | Tours East Africa | |
| 1908 | Promoted to cabinet | |
| Marries Clementine Hozier | ||
| His alliance with Lloyd George | ||
| They declare war on House of Lords | ||
| 1910 | WSC becomes home secretary | |
| His welfare-state programs | ||
| 1911 | Battle of Sidney Street | |
| WSC becomes first lord of the Admiralty | ||
| Father of the tank | ||
| 1912–14 | Irish Home Rule crisis | |
| 1913 | WSC learns to fly, founds Royal Naval Flying Corps | |
| 1914 | Outbreak of the Great War | |
| WSC commands defense of Antwerp | ||
| 1915 | The Dardanelles tragedy | |
| WSC dismissed from the Admiralty | ||
| Learns to paint | ||
| Commissioned and sent to the front | ||
| 1916 | As a lieutenant colonel, leads a battalion in trenches | |
| 1917 | Cleared by the Dardanelles Commission | |
| Rejoins cabinet | ||
| His tanks in action on the western front | ||
| 1918 | WSC in the trenches again | |
| Germany surrenders | ||
| 1919 | WSC becomes secretary for war and air | |
| Chief supporter of Russian anti-Bolsheviks | ||
| 1920 | Black and Tans in Ireland | |
| 1921 | WSC becomes colonial secretary | |
| Lawrence of Arabia his adviser | ||
| Founds Jordan, Iraq | ||
| Supports Jewish homeland | ||
| The Chanak crisis | ||
| WSC founds Irish Free State | ||
| Death of Marigold Churchill | ||
| 1922 | WSC buys Chartwell | |
| 1922–24 | Loses three elections | |
| Turns Tory, wins | ||
| Becomes chancellor of the Exchequer | ||
| 1924 | Warns of danger in Germany | |
| 1925 | Returns Britain to the gold standard | |
| 1926 | General strike | |
| WSC publishes British Gazette | ||
| 1929 | Tours United States | |
| Loses fortune in Wall Street | ||
| 1931 | Quits Tory leadership over India | |
| Manhattan auto accident | ||
| WSC sounds alarm over Nazis | ||
| 1932 | Enters the political wilderness |