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| 1906 |
| | | Harold Macmillan wins a scholarship to the prestigious British public school Eton College | |
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| 1912 |
| | | Harold Macmillan goes to Oxford University, after winning a place in Balliol College | |
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| 1914 |
| | | Harold Macmillan joins the King's Royal Rifle Corps, transferring a few months later to the Grenadier Guards | |
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| 1915 |
| | | Harold Macmillan sees action for the first time in the battle of Loos and is wounded | |
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| 1916 |
| | | After returning to his battalion in April, Harold Macmillan is lightly wounded during a reconaissance patrol | |
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| 1916 |
| | | At the battle of the Somme, Harold Macmillan is seriously wounded in the pelvis and thigh | |
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| 1916 |
| | | Hlding for a day in a shell hole in no man's land, Harold Macmillan reads 'intermittently' the book in his pocket – Aeschylus's Prometheus in Greek | |
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| 1920 |
| | | Harold Macmillan marries Lady Dorothy Cavendish, daughter of the duke of Devonshire | |
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| 1920 |
| | | After his marriage, Harold Macmillan leaves the army and joins the family publishing firm | |
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| 1923 |
| | | Harold Macmillan stands as the Conservative candidate for the Liberal seat of Stockton-on-Tees and is defeated by 73 votes | |
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