August 1640: The Second Bishops' War. The English "New Army" under the Earl of Stafford is pushed back through Northumberland and the Scots under Alexander Leslie take Newcastle on 28 August. Meanwhile the Covenanters take both Edinburgh and Dumbarton castles; and the Duke of Argyll attacks the royalist clans in the Highlands.
12 September 1640: The death in London of Sir William Alexander, 1st Earl of Stirling, the Royal courtier and poet who established Nova Scotia.
26 October 1640: Hostilities cease with a truce signed at Ripon, under which Charles I agrees to pay the costs of keeping their army in northern England.
3 November 1640: King Charles I convenes the English Parliament to raise the funds to settle with the Scots as agreed at Ripon. This "Long Parliament" will to sit until 1653 and lead to Charles' loss of his throne and his head.
October 1641: The weakness of Charles in Scotland leads to Catholic revolt in Ulster, only suppressed with help from Protestant troops from Scotland.
22 August 1642: Charles I, having failed to suppress or coerce the English Parliament by his will, takes it on by military might. The English Civil War begins.
17 August 1643: Scotland offers to support the Parliamentary side in the Civil War in return for the acceptance by the English of a "Solemn League and Covenant", in effect exporting Presbyterianism to them. Military aspects are settled quickly and the English Parliament later accepts the religious aspects of the Covenant.
19 January 1644: A Scottish Covenanter army of 20,000 men under the command of Alexander Leslie moves south to support the Parliamentary Army.
2 July 1644: The Parliamentary Army, reinforced by the Scottish Covenanters, defeat the Royalists at the Battle of Marston Moor.
August 1644: Alasdair MacDonald lands on the Ardnamurchan Peninsula with 2000 troops from Ireland, who are quickly joined by a thousand highlanders. He supports the Royalist cause against Clan Campbell and storms through Argyll before joining forces with the Marquis of Montrose in Perthshire.
September 1644: MacDonald and Montrose defeat a large Covenanter force before taking Perth. They then take on and beat another larger force before taking and pillaging Aberdeen then retreating, pursued by the Marquis of Argyll.
13 September 1644: The Battle of Aberdeen between Royalists and Covenanters is followed by the sacking of Aberdeen by the victorious Royalist forces.
December 1644: Montrose, supported by a reinforced Alasdair MacDonald, attacks Inveraray and the Campbell strongholds of Argyll killing a thousand Campbell Clansmen. They then withdraw north through the highland winter to Inverlochy Castle, near Fort William.
2 February 1645: The 1st Marquess of Montrose makes a forced march south and surprises the Campbells at Inverlochy Castle. Though outnumbered Montrose soundly defeats the Covenanters, killing 1,500 for the loss of far fewer men.
9 May 1645: The Marquis of Montrose and his Royalists camp at Auldearn near Nairn, while en route to attack Inverness. The Covenanters, reinforced by troops withdrawn from England because of the threat from Montrose, gather at Inverness before marching overnight in an attempt to surprise Montrose at Auldearn. After a fierce fight the Royalists again win, killing 2,000 Covenanters for the loss of 200 of their own men.
14 June 1645: The New Model Army, with Oliver Cromwell as its second-in-command, wins the decisive victory of the Civil War at Naseby.
2 July 1645: The Marquis of Montrose and the Royalists again defeat the Covenanters at the Battle of Alford, in Aberdeenshire, but this time with considerable loss of life on both sides. Montrose has defeated the Covenanters throughout northern Scotland.
15 August 1645: At the Battle of Kilsyth, midway between Stirling and Glasgow, Montrose and the Royalists again defeat the Covenanters, killing 3,000. He moves on to capture Glasgow and Edinburgh, effectively controlling Scotland.
5 May 1646: Charles I surrenders to Scottish Covenanters besieging Newark on Trent. The Scots forces take him to Newcastle and try to bargain with him for Scots advantage. The English Parliamentary army threatens to take the King from the Scots by force.
30 January 1647: The Scottish Covenanters march north and back to Scotland having handed Charles I over to the English in return for a payment of £200,000.
30 January 1649: Charles I is executed in London despite protests from the Scots.
5 February 1649: The Scots Parliament proclaims Charles II as King.
March 1649: The English Parliament declares England to be a Republic.
March 1649: A delegation of Scots meets Charles II in the Hague demanding he impose Presbyterianism in Scotland, England and Ireland. Charles refuses.
March 1650: In a last effort to regain power by military means, Charles II seeks help from the Marquis of Montrose, who lands in Orkney with 500 Scandinavian mercenaries before moving on to Caithness, reinforced by Orcadian volunteers.
27 April 1650: At the Battle of Carbisdale, near Bonar Bridge, James Graham, 1st Marquess of Montrose is defeated with heavy losses by a much smaller Covenanter force under Colonel Strachan. Montrose escapes north-west until he is tricked into captivity at Ardveck Castle, on the shore of Loch Assynt.
23 June 1650: Charles II lands at Garmouth in Morayshire after sailing from the Netherlands and evading the English ships trying to intercept him. Charles signed the Covenant and the Solemn League immediately after coming ashore.
3 September 1650: The Battle of Dunbar is a resounding victory for Cromwell, largely because of the actions of extreme religious factions on the Scottish side. Cromwell then marches on Edinburgh and subsequently occupies much of southern Scotland.
14 November 1650 (Gregorian calendar): The birth in the Netherlands of William of Orange, who became King William III of England and of Ireland on 22 January 1689, and King William II of Scotland on 4 April 1689.
July 1651: Cromwell lands a force in Fife that defeats the Scots at Inverkeithing. He then moves on to Perth, tempting Charles II to use the gap he has left to advance on England and claim the throne. Charles takes the bait and Cromwell follows.
22 August 1651: Charles II reaches Worcester with very little evidence of English Royalist support.
3 September 1651: Cromwell attacks Charles II and the Scots Royalists defending Worcester and inflicts a heavy defeat on them. Charles Stewart manages to escape: many of the Scots including Major-General David Leslie do not.
15 October 1651: Charles II sails to France from Sussex after six weeks as a fugitive in England.
4 February 1652: Cromwell's "Tender of Union" is announced in Edinburgh. This gives Scots 30 seats in a united Parliament in London. General Monck becomes Military Governor of Scotland and builds a series of defenses to ensure continued control over the country.
26 May 1652: The last Royalist stronghold anywhere on the eastern side of Scotland, Dunnottar Castle near Stonehaven, surrenders after an eight month siege, though not before the Scottish crown jewels have been smuggled out to safety in Kinneff Old Church.
16 December 1653: Oliver Cromwell is sworn in as Lord Protector of England, Scotland, and Ireland.
19 July 1654: A Royalist uprising in the Highlands led by the Earl of Glencairn and Major-General John Middleton disintegrates after meeting troops under General Monck at the Battle of Dalnaspidal near Loch Garry.
1657: George Fox comes to Scotland as a missionary for the Quaker Society of Friends.
3 September 1658: Oliver Cromwell dies. His son, Richard Cromwell is unable to maintain the Protectorate and resigns in Spring 1659.