Battle of Philiphaug

The Covenanter's army, led by Major-General Sir David Leslie met against Montrose, Captain-General and Lieutenant Governor of Scotland at Philiphaugh. Montrose had been ordered to bring the Covenanters under control. After an unsuccessful invasion of Scotland, Montrose gathered from the Highlands and Ireland a small Royalist force. In a campaign between1644-1645 he repeatedly defeated Argyll's army of Lowland Presbyterians using guerrilla tactics, even when outnumbered (Tippermuir, Inverlochy, and Kilsyth most notable).

In a meadow outside Philiphaugh, Montrose found a strategic location where his army set up camp. They were flanked by a river on the left and a large hill on the right. He and his officers felt secure in this choice, as they left to find more comfortable quarters in Selkirk, the neighboring town. The commander felt confident that after six victorious battles, the enemy troops were demoralized and weakened. Leslie's Covenant army, four times as large as Montrose Royalists, attacked in the moonlight and massacred the unsuspecting men.