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| 1874 | Birth |  |
| 30th Nov Birth of Winston Churchill, Blenheim Palace, family estate near Woods tock, Oxfordshire |
| 1895 | Queen's Own Hussars Churchill |  |
| Commissioned in the 4th Queen's Own Hussars just after his father's death |
| 1896 | Malakand Field Force |  |
| Malakand Does military service with the Malakand Field Force in India's north-western frontier |
| 1898 | Campaign Sudan |  |
| London Undertakes military service in the Sudan Campaign |
| 1899 | Arrest |  |
| Colenso Taken prisoner by the Boers after the derailment of his armoured train near Colenso |
| Nov Pretoria Arrested, asked to be released because he is a correspondent but refused |
| 15th Nov Escourt Leaves Escourt in a train commanded by Captain Haldane to explore Boer positions |
| 12th Dec Colenso Makes a dramatic escape from the Boers which reaches the world's headlines |
| 12th Dec Pretoria The Boers offer œ25 for Churchill dead or alive |
| 23rd Dec Durban Reaches Durban & describes his escape to an enthusiastic crowd |
| 1899 | Battle of Spion Kop |  |
| Sion Kop Takes part in the battle of Sion Kop |
| 1899 | Bounty Churchill |  |
| 12th Dec Pretoria The Boers offer œ25 for Churchill dead or alive |
| 1899 | Correspondence Boers |  |
| 29th Dec London Says that 1 Boer soldier is worth 3 British |
| 1899 | Election |  |
| 7th July Oldham Fails in his first attempt to be elected to Parliament, defeated by 1,300 |
| 1899 | Escape Churchill |  |
| 23rd Dec Durban Arrives at Durban, highlight of a "black week"during the Boer War |
| 23rd Dec Durban Hailed a hero & begins his political career |
| 1899 | Publication |  |
| Publication of, "Savrola", serialised in "MacMilan's Magazine" for a fee of œ100 |
| 1899 | Resignation |  |
| Mar Resigns his commission & leaves India |
| 1899 | Siege of Ladysmith |  |
| Ladysmith Serves in the force which relieves Ladysmith |
| 1899 | War Correspondent |  |
| Appointed War correspondent in Sth Africa for The Morning Post |
| Goes to Sth Africa as a military correspondent for the Daily Telegraph |
| 14th Oct Leaves on the Dunnotar Castle for Sth Africa as a War Correspondent for the Daily Mail |
| 1900 | Battle of Spion Kop |  |
| Spion Kop At the Battle of Spion Kop |
| 1900 | Battle of Tugela River |  |
| 17th Feb River Tugela Fights at the battle of Tugela |
| 1900 | Capture of Orange FS |  |
| Orange Free Marches through the Orange Free State with Lord Roberts |
| 1900 | Capture of Pretoria |  |
| June Pretoria Present at the British entry into Pretoria |
| 1900 | Defection |  |
| 12th Dec Oldham Churchill has decided to join the Liberal Party |
| 12th Dec Oldham Informs his constituency he will not contest the next election |
| 20th Dec Ludlow Supports the prospective Liberal Party candidate at the Ludlow by-election |
| 31st Dec Dines with Lloyd George to sound him out about joining the Liberal Party |
| 1900 | Election |  |
| 1st July Oldham Churchill claims "a seat lost to the government is a seat gained to the Boers " |
| 1st July Oldham Elected Member of Parliament for Oldham |
| 1900 | Lieutenant Sth Afr Light |  |
| Appointed Lieuetenant in the SouthAfrican Light Horse |
| 1900 | Member of Parliament |  |
| 25th July Oldham Appointed Prospective MP for Oldham |
| 1900 | Publication |  |
| 15th May Publication of, "London to Ladysmith via Pretoria" |
| 1901 | Defection |  |
| Jan Lunches with Herbert Gladstone to discuss seats for himself as a Liberal MP |
| 1901 | Resignation |  |
| Resigns from the Conservatives & joins the Liberals on the issue of free trade |
| 1901 | Speech |  |
| 18th Feb London Churchill makes his maiden speech in the House of Commons |
| 1902 | Publication |  |
| Begins work on the official biography of his father |
| 1903 | FFL |  |
| May Founds the Free Food League with Conservative MP's in favour of free trade |
| 1903 | Free Trade |  |
| Supports Free Trade & opposes Chamberlain's policy of Imperial Preference |
| 1903 | Speech |  |
| 24th Feb London Speaks in the Commons against the government's proposed increase in military spending |
| 25th May Hoxton Supports Free Trade in answer to Chamberlain's speech in favour of Imperial Preference |
| 27th May London Attacks his party's proposals to increase military expenditure |
| 28th May London Rebukes Chamberlains speech on Imperial Preference in the Commons |
| 1904 | Defection |  |
| Jan The Conservative whip is withdrawn because of his support Liberal support |
| 14th Feb Votes with the Liberals against his own party on a Free Trade motion |
| 29th Mar London There is a walkout of Conservative MP's when Churchill stands up to speak |
| 31st May London Cross es the House of Commons to become a Liberal |
| 1904 | Free Trade |  |
| Supports free trade with the Liberals as an independent MP |
| 1904 | Liberal Candidate |  |
| April Manchester Adopted as a Liberal Candidate in Manchester North West |
| 1904 | Liberal Party |  |
| 31st May Manchester Sits on the opposition benches for the 1st time |
| 1904 | Reform |  |
| Manchester Defends his Jewish constituents in Manchester by objecting to the Aliens Bill |
| 1905 | Election |  |
| 9th Dec Offerred the post of Financial Secretary at the Treasury, prefers a smaller department |
| 1905 | Speech |  |
| 13th May Manchester Describes the Conservative Party as a party of "great vested interests" |
| 4th June Manchester Supports Free Trade while speaking at a mass meeting in Manchester |
| 10th Dec Manchester Speaks against the persecution of Jews in Russia at the |