The Battle of Lochmaben Fair represented a significant conflict during a period of unstable power dynamics in Scotland. On this occasion, Alexander Stewart, the Duke of Albany, and James Douglas, the 9th Earl of Douglas, launched a raid with a force of approximately 500 men. Their intention was to assert dominance and influence over regions loyal to the Scottish crown, particularly as a challenge to King James III, the brother of Alexander Stewart. The encounter took place against the backdrop of the broader political upheaval during the late 15th century in Scotland, a time when factions often clashed for control and allegiance.

The loyalist forces, who rallied in defense of King James III, swiftly organized a counter-strategy, capitalizing on their knowledge of the terrain and the element of surprise. During the clash near Lochmaben, they effectively engaged Albany and Douglas’s forces, leading to a comprehensive defeat of the raiding party. A notable outcome of this confrontation was the capture of James Douglas, a significant noble, which not only deprived Albany of an essential ally but also strengthened the position of King James III.

The repercussions of the battle extended beyond the immediate conflict. It illustrated the volatility of noble alliances and the precariousness of power among Scottish nobility. The king's loyalists demonstrated their strength, setting a precedent for further confrontations between loyalist and rebellious factions in Scotland's turbulent political climate. Such skirmishes were common during this period, as the interplay of royal authority and noble independence often led to further discord across the Scottish landscape.