In 1391, King Robert II's reign was largely entrusted to his sons, Robert Stewart, Earl of Fife, and Alexander Stewart, Earl of Buchan.^[2] The latter, known as the “Wolf of Badenoch”, effectively sidelined his father, and operated with cruelty and terror.^[3]

Following the plunder of lands belonging to Alexander Bur, Bishop of Moray, and the burning of the Bishop's Cathedral at Elgin,^[4] his son, Duncan Stewart, led a raiding force of Robertsons into Angus, where they burned, pillaged, and slaughtered.^[5] The raiders first attacked Glen Isla and Glen Esk, and in response, a small local force gathered and attacked at Glasclune.^[5] A bloody battle ensued, but the local force failed to stop the invading Robertsons, and the raiding continued up the Strathardle.^[5] Duncan Stewart was also apparently supported by Angus Mackay, 6th of Strathnaver, whose aunt, Mariota Mackay, was the wife of Alexander Stewart, Earl of Buchan.^[1]

As Sheriff of Angus, Sir Walter Ogilvy of Auchterhouse gathered a force including his allies Sir Patrick Gray and Sir David Lindsay, and confronted the raiders at Dalnagairn, Glen Brierachan.^[5] Though charging with cavalry with heavy armor and lances, the Ogilvys were outnumbered, and Sir Walter Ogilvy, several lairds, and nearly sixty followers perished.^[5] Gray and Lindsay were seriously wounded in the fighting, but survived.^[5] An account of the battle by Andrew of Wyntoun said the following about Sir Walter Ogilvy: "Gud Schir Walter off Ogylvy, That manly knycht and that worthy Scherrave that tyme off Angus, Godlike, wis, and vertuous...."^[6]

• Clan Ogilvy