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Assume history stays the same unless mentioned.
84 - Roman invasion of Caledonia. It is slowly 'Romanised'.
122 - Building of Hadrian's wall. It is built to halt a potential rebellion marching south, although this would never materialise.
383-410 - Roman withdrawal from Britain. Anglo-Saxons begin settlement in England, and Picts begin moving south of the border.
450-500 - Skirmishes with Picts mean that the Anglo-Saxons are forced to move south. The kingdoms of Bernicia never materialises and is instead settled by Picts and Scots along with northern Deira. Other forming kingdoms are also overrun.
843 - Unification of Scotland.
927 - Unification of England.
930 - Pict Uprising.
1066 - Norman conquest of England. Scotland is not invaded but would be influenced by the Normans.
1296-1328 - English invasion of Scotland (First War of Scottish Independence). It fails and ends with the Treaty of Edinburgh-Northampton, merging the lands settled by Picts but claimed by England into Scotland.
1332-1357 - Discontent after the signing of the treaty leads the the Second War of Scottish Independence which again fails. The Treaty of Berwick is signed.
1480-1493 - First War of English Indpendence. Scotland attempts to invade England, getting as far as Birmingham but are fought back. Some Scottish border gains are made but overall the war is inconclusive.
1513 - James V of Scotland declares himself King of Ireland.
1532-1544 - Second War of English Independence. The war ends in an unconditional English victory.
1569 - War between Scotland and Denmark for control of the German Ocean (now North Sea) . A small and unprepared Scottish fleet is defeated.
1579-1582 - English uprising. This spirals into the 5th Anglo-Scottish War. English rebel strongholds like Newcastle revolt and join England, creating the 'Second Kingdom'.
1591-1593 - 6th Anglo-Scottish war and the conquest of the Second Kingdom. Lands in the North are annexed to Scotland, and England and Scotland are ruled by James I in 'the Union of the Crowns'.
1542-1651 - English civil war ends in the execution of Scottish Charles I.
1652-1688 - Series of wars between England and the Dutch over trade with England's last colonies. A pro-Scottish Dutch lord ends up on the throne of England - William III of Orange-Nassau. He intends to unify England and Scotland, then convince the Dutch King to enter a union with the new country.
1700 - Success of the Darien scheme and colonisation attempts in North America means Scotland becomes steadily richer, whilst England is plummeted into new economic hardships.
1707 - Act of union between Scotland and England.