Battle of Philiphaugh The Battle of Philiphaugh was fought on 13 September 1645 during the Civil War near Selkirk in the Scottish Borders . The Royalist army of the Marquis of Montrose was destroyed by the Covenanter army of Sir David Leslie , restoring the power of the Committee of Estates . Prelude . When the Covenanters became allies of the English Parliamentarians , Montrose was given a commission as King Charles ' s Lieutenant General in Scotland . He was able to raise an army consisting of regiments of Irish soldiers sent to Scotland by the Irish Confederates and shifting numbers of Highland clansmen . With these troops , Montrose had won a remarkable series of victories in the year preceding the Battle of Philiphaugh . The last of these was at Kilsyth , which destroyed the last Covenanter army in Scotland and put the lowland towns at his mercy . Montrose refused to allow his army to loot Glasgow , instead accepting a sum of £500 from the Town Council as pay for his soldiers . He then summoned a Parliament to be held in Glasgow . The Council complained at the cost which would be involved and asked to be excused the levy of £500 . Montrose agreed , leaving his army without pay . Although Montrose intended to strike into England to aid the King ' s cause there , the Highlanders under Alasdair MacColla who made up most of Montrose ' s infantry refused to go any further south leaving their traditional foes , the Campbells , in their rear . At the same time , Montrose appointed the former prisoner , the Earl of Crawford as his Lieutenant General of Horse . Most of his horsemen were Gordons under Lord James Aboyne . Affronted by Crawford ' s appointment , they too left the army . Montrose hoped to gain recruits from the Borders , and marched south with only 500 musketeers from his Irish Catholic regiments and a small troop of horse . He made for Kelso , but found that only a few Borders gentry joined his army instead of the thousands of recruits he expected . Meanwhile , the Earl of Leven , who commanded the main Scottish Covenanter Army in England , had heard of the result of the Battle of Kilsyth , and sent Sir David Leslie , the Lieutenant General of Horse , back into Scotland with all the cavalry he could muster . Leslie collected reinforcements from Covenanter garrisons in Newcastle upon Tyne and Berwick , and crossed the border on 6 September , with 5000 horse and dragoon s and 1000 infantry . He marched along the east coast intending to cut off Montrose from the Highlands , but learned ( possibly from the turncoat Earls of Home and Roxburgh ) of Montrose ' s position and strength , and turned south to intercept him . Battle . Contemporary accounts give only a broad outline of the battle . Subsequent authors have interpreted this in various ways in an attempt to arrive at a more detailed account . Montrose himself , many of his officers and some of the cavalry were quartered in the town of Selkirk , with the infantry and the rest of the cavalry encamped on flat ground the other side of the river ( the Ettrick Water ) at Philiphaugh . Warner puts this just below the junction of the Yarrow Water and the Ettrick Water and hence about away . However , a contemporary description of the Royalist infantry position has them behind " on one hand an unpassable ditch , and on the other Dikes and Hedges , and where these were not strong enough , they further fortified them by casting up ditches , and lined their Hedges with Musketeers " , hence other interpretations would put the royalists within field enclosures shown on an 18th - century map between and from Selkirk . Leslie had arrived at nearby Melrose the evening before , and advanced up the valley of the Tweed , driving in the Royalist outposts at Sunderland ( at the junction of the Ettrick Water with the Tweed , about downstream of Selkirk ) without apparently alarming or alerting the main Royalist force . The following morning was misty , and whatever scouting was undertaken by the Royalists failed to reveal the presence of Leslie ' s forces . Leslie divided his force into two wings , one of which attacked the Royalist position directly , getting to within half a mile before the alarm was raised . The other executed a flanking manoeuvre , probably on the south bank of the Ettrick Water although some interpretations follow a later ballad and say through hilly ground to the north . Montrose was alerted to Leslie ' s attack by the sound of gunfire , but arrived on the battlefield to find his forces in considerable confusion . Although the Royalist infantry ' s strong defensive position enabled them to repel at least two Covenanter attacks , the arrival of Leslie ' s flanking force ensured their defeat . After Montrose made a brief attempt to restore the situation by charging 2 , 000 Covenanter dragoons with only 100 cavalry of his own , he was urged by his friends that the Royalist cause in Scotland would die without him . He cut his way out with 30 men , and retreated over the Minchmoor road toward Peebles . Many of Montrose ' s Irish foot soldiers from Manus O ' Cahan ' s regiment had been killed in the battle , but after fighting on for some time after the flight of the cavalry about 100 of them surrendered on promise of quarter . Some Presbyterian Ministers who accompanied Leslie persuaded him that this clemency was foolish , and the prisoners and 300 camp followers ( many of them women and children ) were slaughtered in cold blood . Aftermath . Montrose attempted to raise another army in the Highlands , but was unable to take the field against Leslie ' s army . After fighting a guerilla campaign over the following winter and spring , he received orders from King Charles ( who was now himself a prisoner ) to lay down his arms . Montrose , Crawford and Sir John Hurry , who had changed sides to join Montrose after the Battle of Auldearn , were refused pardon by the victorious Committee of Estates and went into exile . Today the ( most likely site of the ) battlefield is home to Selkirk Cricket Club and Selkirk Rugby Club , along with a small number of cottages . The site of the battle has been inventoried and protected by Historic Scotland under the Scottish Historical Environment Policy of 2009 .