Early Life
| Date | Event |
| 25 Apr 1599 | Born Huntingdon |
| 1616 | Enters Sidney Sussex College, Cambridge University |
| June 1617 | Oliver Cromwell’s father dies; Cromwell leaves University to return to Huntingdon |
Early Adult Life
| 22 Aug 1620 | Marries Elizabeth Bourchier at St. Giles, Cripplegate, London |
| 1628 | Elected Member of Parliament for Huntingdon |
| 1629 | Charles I decides to rule without calling an English parliament, beginning an 11 year period of Personal Rule |
| 1640 | Personal rule collapse and Cromwell re-enters parliament as MP for Cambridge |
English Civil War Years
| 1642 | Start of the English Civil War |
| 1642 | Cromwell joins the side of the Parliamentarians (or “Roundheads”), raises a troop of cavalry in Huntingdon |
| 23 Oct 1642 | Battle of Edgehill |
| 1643 | Appointed to the post of Colonel in the Eastern Association Army |
| 30 Jun 1643 | Battle of Adwalton Moor |
| 13 Jul 1643 | Battle of Roundaway Down |
| 20 Sep 1643 | First Battle of Newbury |
| 1644 | Promoted to the post of Lieutenant-General of the Eastern Association Army |
| 02 Jul 1644 | Battle of Marston Moor |
| 27 Oct 1644 | Second Battle of Newbury |
| 06 Jan 1645 | The New Model Army is created, under the leadership of Commander-in-Chief Sir Thomas Fairfax |
| 1645 | Cromwell is appointed to the post of Lieutenant-General of the New Model Army |
| 14 Jun 1645 | Battle of Naseby |
| Jul 1645 | Cromwell takes over command of Bartholomew Vermuyden’s Regiment after Vermuyden resigns |
| 1647 | Having failed to reconcile King Charles I, Parliament and the army, Cromwell supports the Parliamentary army in clashes with Parliament |
| 1648 | Crushes Royalist rising in South Wales |
| 18 Aug 1648 | Battle of Preston (Cromwell’s army defeat the Royalists) |
| 1648 | Cromwell pushes for the trial of Charles I, for treason |
| Jan 1649 | Cromwell becomes one of the signatories of the king’s death warrant |
| 30 Jan 1649 | Charles I is executed |
| Jan 1649 | The monarchy is replaced by the Council of State of the Commonwealth |
| Aug 1649 | Leads an army sent to crush Ireland, defeating the Confederate and Royalist coalition and occupying the country, ending the Irish Confederate Wars |
| Jun 1650 | Cromwell is appointed Captain-General of the Commonwealth |
| Jul 1650 | Leads an army sent to crush Scotland |
| 03 Sep 1650 | Battle of Dunbar |
| 03 Sep 1651 | Battle of Worcester |
| 20 Apr 1653 | Dissolves the Rump Parliament by force, setting up the short-lived Barebone’s Parliament |
Lord Protector
| 16 Dec 1653 | Cromwell is invited by his fellow leaders to become Lord Protector of England, Wales, Scotland and Ireland |
| 1654 | Sends the navy to the West Indies which seized Jamaica |
| Sep 1654 | Meets first Protectorate Parliament |
| May 1655 | England begins to be divided into separate groups of counties, under the command of individual Major-Generals |
| Sep 1656 | Meets the second Protectorate Parliament |
| 1657 | System of the Major-Generals is ended |
| Mar – Jun 1657 | Rejects Parliament’s offer of the crown and remains Lord Protector |
| 03 Sep 1658 | Cromwell dies at Whitehall, having succombed to a malarial desease, and to septicaemia caused by a kidney-stone induced urinary infection |
| 03 Sep 1658 | Cromwell’s son Richard succeeds him as Lord Protector |
| Nov 1658 | Cromwell receives a ceremonial state funeral at Westminster Abbey |
| May 1659 | Richard Cromwell is forced to resign his post |
| 1660 | The monarchy is restored to England under the rule of Charles II |
| 30 Jan 1661 | The Royalists exhume Cromwell’s body and and posthumously ‘execute’ him, hanging his body in chains and beheading his corpse |
| 1661 | Cromwell’s body is buried at Tyburn (now Marble Arch) |