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| • 1599 | April 25th - Oliver Cromwell is born in the Cambridgeshire town of Huntingdon to Robert and Elizabeth Cromwell. |
| • 1620 | August 22nd - Cromwell marries Elizabeth Bourchier whose father is a wealthy merchant. The marriage brings Cromwell into contact with wealthy London merchants and great Puritan peers. |
| • 1628 | Cromwell becomes the Member of Parliament for Huntingdon. |
| • 1629 | March - Charles dissolves parliament and imprisons eight parliamentary leaders who are opposing his will. |
| • 1633-1635 | King Charles raises taxes called 'ship money' - pretending they are to fight pirates; but demands it inland as well as on the coast and takes people's goods if they have no money. Many people are angry. |
| • 1636 | Oliver, who is now a Puritan, inherits a place and a job from his uncle in Ely. |
| • 1637-8 | King Charles tries to force the book of common prayer on an unwilling Scotland, gathers an army and starts the 'Bishop's war'. |
| • 1640 | Charles summons Parliament, but they refuse to grant him money for his war so he dissolves it again. |
| | November 3rd - The king summons Parliament again, because he needs money. It declares the 'ship tax' illegal amongst other popular reform measures. |
| • 1641 | An uprising in Ireland has Parliament and King agreeing they need an army but not trusting each other to lead it. The Grand Remonstrance, which lists all the grievances Parliament has about the king's actions over the years, is handed to the king. |
| • 1641-42 | Parliament proposes it should appoint the commanders of the army, the king refuses and tries to arrest 5 members of Parliament but fails. He is so unpopular that he flees London and sets up court in York. |
| • 1642 | Parliament votes in a 'Militia Bill' to defend the nation without the king's consent. The king uses an old law to issue a 'Commission of Array' allowing him to raise emergency forces. |
| | June - Parliament passes The Nineteen Propositions and send them to the king in York. They require the king to give up control of the militia and the right to appoint ministers. He refuses. |
| | August 22nd - The English Civil War officially begins when King Charles raises the royal standard at Nottingham Castle. King and Parliament are now at war. |
| • 1642-3 | Cromwell raises and leads cavalry troops for Parliament and is recognised as a good leader. |
| • 1644 | Victory at Marston Moor fails to crush finally the King's armies. Cromwell pushes Parliament for better commanders and better trained troops. |
| • 1645 | The New Model Army is created by parliament. It is a professional, trained, military unit. Commander-in-chief is General Fairfax. Oliver Cromwell, as Lieutenant-General, is put in charge of the cavalry. At the Battle of Naseby, the New Model Army inflicts a crushing defeat on the king's army. |
| • 1646 | June 24th - At Oxford, the New Model Army beseige the Royalists who surrender and the first civil war ends. |
| • 1647 | The Scots hand over Charles to the Parliamentarians and withdraw from England. He is held as a prisoner at Holmby House in Northamptonshire, where he continues to plot for the restoration of his power. The Parliamentarians disagree about the ways forward amongst themselves. |
| | November - Charles flees to the Isle of Wight and makes a pact with the Scots to attack England and starts the second Civil War. |
| • 1648 | The king rejects Parliament's suggestions for peace. Cromwell leads the New Model Army, crushes Royalists in Wales and then the Scots' invasion. The Second Civil War finally ends on 28th August. |
| • 1649 | Many in Parliament have lost all trust in King Charles because his plotting started the second war. They establish a High Court of Justice to try King Charles I for treason. He is found guilty on January 27th. |
| | January 30th - King Charles 1 is beheaded. |
| | On 18th May an Act is passed declaring England to be a Commonwealth. The Scots and Irish declare they intend to help Charles II to become king.
August - Cromwell leads an army to Ireland. At Drogheda and Wexford, Cromwell's troops massacre the Royalist garrisons as well as civilians, following their capture of the towns.
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| • 1650 | Cromwell takes the New Model Army to Scotland after the Scots proclaim Charles I's son to be King Charles II. Cromwell completely defeats the Scottish army at Dunbar. |
| • 1651 | The Scottish army,led by Charles II, slips south while Cromwell is in Scotland. Cromwell follows and destroys them at the Battle of Worcester, the final battle of the Civil Wars. Charles flees to exile in Holland. |
| • 1653 | Angered that Parliament are stopping reforms, Cromwell and his army march into parliament and forcibly dissolve it. |
| | December 16th - Cromwell reluctantly becomes Lord Protector. |
| • 1658 | September 3rd - Oliver Cromwell dies at Whitehall in London, probably from malaria or from blood poisoning following an infection. |
| • 1660 | King Charles II is restored to the throne |