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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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| 1924 |
| | | Harold Macmillan stands again for Stockton-on-Tees and this time wins the seat with a majority of 3215 | |
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| 1929 |
| | | In the general election Harold Macmillan loses Stockton-on-Tees to the Labour candidate, Frederick Riley | |
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| 1929 |
| | | Harold Macmillan's wife begins a long affair with Conservative MP Robert Boothby, but Harold Macmillan decides against divorce | |
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| 1931 |
| | | Harold Macmillan recovers the parliamentary seat of Stockton-on-Tees | |
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| 1938 |
| | | Harold Macmillan publishes The Middle Way, outlining a practical course of political action largely based on the ideas of Keynes | |
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