The Royal Burgh of Lochmaben is located at the north end of Castle Loch, about 10 miles northeast of Dumfries. The most important aspect of this raid on the town, named the Battle of Lochmaben, was that for the first time in Scotland's history, loyalty to the Crown took precedence over loyalty to the local feudal overlord.

Ever since Archibald Douglas laid siege to the Lochmaben castle in 1384 and captured it from the English, the Douglas family's power was a constant thorn in the Scotland Crown's side. After James III defeated the Douglas at the Battle of Arkinholm near Langholm, about 1470, Lochmaben castle came under the control of the Scotland Crown.

Alexander, the Duke of Albany, was also the younger brother of King James III. More warlike than his brother, whose favorites were more talented in the arts of peace, Albany had been exiled from Scotland. At the English court, he met James, Earl of Douglas, who also had fled to England after Arkinholm. The English king, Edward IV, promised his assistance to Albany who was to be made King of Scotland while owing allegiance to Edward. Edward was to be given the towns of Berwick and Lochmaben, with the lands of Liddesdale, Eskdale and Annandale. Albany was to marry Edward's daughter Cecily.

With Edward's help, these plans might have succeeded. But Edward died, and his successor, Richard III, withdrew his support. This left Albany's main hope in gaining the throne of Scotland to be his alliance with the aging Douglas and the loyalty of Douglas' retainers as they advanced north of the border.

On June 22, 1484, a force of renegade Scots including the Earl of Douglas, and English soldiers under Albany, crossed the border in an attempt to capture Lochmaben.