The fortunes of the chiefly family were established in February 1380, when John Rollok, secretary to David, Earl Palatine of Strathearn and brother of King Robert II of Scotland, received a charter from the king of the lands of Duncrub. His son, Duncan Rollo of Duncrub, was Auditor of State Accounts until his death in 1419.
William Rollo of Duncrub received a charter on 26 August 1511, erecting his lands into a free barony. He is thought to have died leading the Clan Rollo at the Battle of Flodden in 1513 along with his elder son, Robert. Andrew Rollo then inherited the estates, and married his cousin, Marion, heir to David Rollo of Manmure. One of his younger sons, Peter, became Bishop of Dunkeld and a judge of the Court of Session. His grandson, Sir Andrew Rollo, was knighted by King James VI of Scotland.
The Clan Rollo were staunch royalist supporters of the king during the civil war. Their loyalty was rewarded when King Charles II created Sir Andrew Lord Rollo of Duncrub in 1651. However, by 1654, Oliver Cromwell was firmly in control of Scotland, and Lord Rollo was fined £1.00,000 for his royal connections.
Lord Rollo’s fifth son, Sir William Rollo, was a gifted soldier and one of James Graham, 1st Marquess of Montrose’s lieutenants. Chief Sir William Rollo led the clan and commanded the left wing of the royal army at the Battle of Aberdeen in 1644, and followed the marquess on his famous forced march over mountainous terrain which surprised the forces of the Marquess of Argyll and led to the royalist victory at the Battle of Inverlochy. When Montrose thrust south, the royalist forces were themselves trapped by an unexpected force of Covenanter cavalry at the Battle of Philiphaugh. Rollo was captured and beheaded at Glasgow in October 1645. It is perhaps indicative of the complex politics of Scotland at this time that William’s brother, James, second Lord Rollo, was married first to the sister of the James Graham, 1st Marquess of Montrose and then to the sister of his rival, the Marquess of Argyll.
Despite Andrew Rollo’s support for William of Orange, his son, the fourth Lord Rollo, was a staunch Jacobite who attended the great hunt at Aboyne in August 1715, which was in reality a secret council to plan the rising of that year. He along with the Clan Rollo fought at the Battle of Sheriffmuir but surrendered. He was imprisoned for a time, but pardoned in 1717. He had seven children, and died peacefully at Duncrub in March 1758.
His eldest son, Andrew, fifth Lord Rollo and chief of Clan Rollo became a professional soldier, although he did not embark upon his career until the relatively late age of forty. During the War of the Austrian Succession he fought for the British at the Battle of Dettingen in 1743, and by 1758 he commanded the British 22nd Regiment of Foot. He was sent to the Americas, where he fought under General Murray in the last campaign to secure Canada as a British possession. In 1759 he was sent to capture the French Caribbean island of Dominica which, although heavily fortified, he took with a force of only two thousand five hundred men. In 1760 he was raised to the rank of brigadier general. He fought for two more years in the Caribbean, during which time both Barbados and Martinique fell to the British. However, his health was severely affected by the climate, and he returned to England in 1762, dying at Leicester in 1765.
Military service continued to draw the Rollos into the ranks, and the seventh Lord Rollo fought with distinction at the siege of Pondicherry in India, commanding a force of marines. John, eighth Lord Rollo, was an officer in the 3rd Regiment of Foot Guards which is today the Scots Guards, and fought on the Continent between 1793 and 1795.
The present chief, David Eric Howard Rollo, the thirteenth Lord Rollo and fourth Baron Dunning, still lives in Perthshire.