Matilda I, Countess of Boulogne in the context of "William I, Count of Boulogne"

Malcolm III (Middle Irish: Máel Coluim mac Donnchada; Scottish Gaelic: Maol Chaluim mac Dhonnchaidh; c. 1031–13 November 1093) was King of Alba from 1058 to 1093. He was later nicknamed "Canmore" (Scottish Gaelic: ceann mòr, lit. 'big head', understood as "great chief"). Malcolm's long reign of 35 years preceded the beginning of the Scoto-Norman age. Henry I of England and Eustace III, Count of Boulogne were his sons-in-law, making him the maternal grandfather of Empress Matilda, William Adelin and Matilda I, Countess of Boulogne. All three of them were prominent in English politics during the 12th century.

Malcolm's kingdom did not extend over the full territory of modern Scotland: many of the islands and the land north of the River Oykel were Scandinavian, and south of the Firth of Forth there were numerous independent or semi-independent realms, including the kingdom of Strathclyde and Bamburgh, and it is not certain what if any power the Scots exerted there on Malcolm's accession. Throughout his reign, Malcolm III led at least five invasions into English territory. One of Malcolm's primary achievements was to secure the position of the lineage that ruled Scotland until the late thirteenth century, although his role as founder of a dynasty has more to do with the propaganda of his descendants than with history. He appears as a major character in William Shakespeare's Macbeth, while his second wife, Margaret, was canonised as a saint in the thirteenth century.

The Anarchy was a civil war in England and Normandy between 1138 and 1153 which resulted in a widespread breakdown in law and order. The conflict was a war of succession precipitated by the accidental death of William Adelin—the only legitimate son of King Henry I—who drowned in the White Ship disaster of 1120. Henry sought to be succeeded by his daughter, Empress Matilda, but was only partially successful in convincing the nobility to support her. On Henry's death in 1135, his nephew Stephen of Blois seized the throne with the help of his brother Henry of Blois, who was the bishop of Winchester. King Stephen's early reign saw fierce fighting with disloyal English barons, rebellious Welsh leaders, and Scottish invaders. Following a major rebellion in the southwest of England, Matilda invaded in 1139 with the help of her half-brother Robert of Gloucester.

In the initial years of civil war, neither side achieved a decisive advantage; Matilda came to control southwest England and much of the Thames Valley, while Stephen remained in control of the southeast. Barons who refused to support either side held much of the country. The castles of the period were easily defensible, so the fighting was mostly attrition warfare comprising sieges, raiding and skirmishing. Armies mainly consisted of knights and infantry, many of them mercenaries. In 1141 Stephen was captured following the Battle of Lincoln, causing a collapse in his authority over most of the country. When Matilda attempted to be crowned queen, she was forced instead to retreat from London by hostile crowds; shortly afterwards, Robert of Gloucester was captured by Stephen's wife, Matilda of Boulogne, at the rout of Winchester. The two sides agreed to a prisoner exchange, swapping the captives Stephen and Robert. Stephen then almost captured Matilda in 1142 during the Siege of Oxford, but she escaped from Oxford Castle across the frozen Thames to safety.