The Battle of Dalnaspidal was the final action of the Glencairn Rising, sometimes called the Royalist insurrection of 1653 to 1654. After the execution of Charles I in 1649 and the failure of the Third English Civil War in 1651, Scotland had been formally incorporated into Cromwell's Commonwealth. But the Highlands were never fully subdued. In 1653 William Cunningham, the 9th Earl of Glencairn, raised a fresh rising in the name of the exiled Charles II. He recruited from clans with old grievances against the Cromwellian-aligned Campbells. Clan MacGregor came in from Rannoch, easily persuaded because one of the opposing commanders was the Earl of Argyll, hereditary chief of the Campbells and hereditary enemy of the MacGregors. Alexander, the 12th chief of Clan Robertson, led his men from Fea Corrie. The two clan forces met above Annat and marched up the old path to Loch Garry, joining a larger Royalist army under John Middleton, who had been sent over from the Continent by Charles II to take overall command.

Thomas Morgan was one of Cromwell's most effective field commanders, a Welsh soldier who had served on the Continent in the Thirty Years War. By July 1654 he was operating in the central Highlands with a strong force of horse and foot. He had been tracking Middleton's army for weeks. On the evening of 19 July, near Dalnaspidal at the head of Loch Garry on the Drumochter Pass, he caught them strung out and unprepared. The Royalist horse, riding ahead, was separated from the foot soldiers coming up behind. Morgan saw the opening and threw his cavalry into the gap. Most of Middleton's mounted men broke and fled, abandoning the infantry. With the foot now unprotected, the Cromwellian horse pressed home its advantage. The Royalist infantry, watching their own cavalry disappear over the hill, lost their nerve and ran too. There was no extended battle. Drumochter is no place for an extended battle: narrow, exposed, heather-and-rock terrain, no cover, no flanks to work. Once the line broke, the rout was complete.

Middleton was wounded but escaped into the mountains. He was never able to gather a substantial force again. The Glencairn Rising was effectively over. General George Monck, Cromwell's commander in Scotland, wanted the leaders of the uprising put to death as an example. The Protector and the Council overruled him. They issued a promise of pardon to all who submitted, formalised in Cromwell's Act of Grace, which was a calculated gesture of conciliation aimed at preventing another rising rather than provoking one through reprisal. William, Earl of Glencairn surrendered to Monck in September 1654. Middleton managed to slip back to the Continent and rejoined Charles II at Cologne in early 1655, where the king was waiting out the rest of the Interregnum. Charles eventually returned to England at the Restoration of 1660, and Middleton with him, ennobled as the 1st Earl of Middleton. The clansmen who had marched up to Drumochter that summer were mostly pardoned and went home. Their commanders survived. Cromwell died in 1658. The Stuart cause, sleeping for now, would wake again in 1715 and 1745.