Battle of Loudoun Hill The Battle of Loudoun Hill was fought in May 1307 between a Scots force led by Robert Bruce and the English commanded by Aymer de Valence . It took place beneath Loudoun Hill , in Ayrshire , and ended in a victory for Bruce . It was Bruce ' s first major military victory . The battlefield is currently under research to be included in the Inventory of Historic Battlefields in Scotland and protected by Historic Scotland under the Scottish Historical Environment Policy of 2009 . A Royal Fugitive . Bruce and Valence had first met in combat the previous year at the Battle of Methven just outside Perth , where Bruce ' s lack of preparedness , and his somewhat conventional military tactics , had brought him to the edge of disaster and beyond . His army virtually disintegrated under Valence ' s rapid onslaught , with many of Bruce ' s leading supporters falling captive . What was left of his force was mauled for a second time soon after this by the Macdougalls of Lorn , allies of the English , at the Battle of Dalrigh . As an organised military force the army of Scotland ceased to exist , and the king took to the heather as a fugitive . For a time he took refuge in Dunaverty Castle near the Mull of Kintyre , but with his enemies closing in once more , he sailed out of the light of history into the mist of legend , seeking refuge on Rathlin Island near the coast of Ulster , according to some , and the Orkney Isles , according to others : into a cave inhabited by a spider . Supposedly , Bruce watched the small spider try to spin a line across a seemingly impossibly wide gap . As Bruce watched , the spider tried and tried and tried . " Foolish spider " thought Bruce , but continued to watch . Suddenly , the spider succeeded in leaping across the gap with its thread . Bruce considered this , and took it as an encouragement that he , too , should continue to persevere regardless of seemingly hopeless circumstances , and he later came out of hiding . It is doubtful if the story is true , however . Return of the King . When he reappeared in February 1307 he was set to take his greatest gamble . From the island of Arran in the Firth of Clyde he crossed to his own earldom of Carrick , in Ayrshire , landing near Turnberry , where he knew the local people would be sympathetic , but where all the strongholds were held by the English . A similar landing by his brothers Thomas and Alexander in Galloway met with disaster on the shores of Loch Ryan at the hands of Dungal MacDougal , the principal Balliol adherent in the region . Thomas and Alexander ' s little army of Irish and Islemen was destroyed , and they were sent as captives to Carlisle , where they were later executed on the orders of Edward I . But against all the odds Robert survived and with remarkable tenacity soon established himself in the hill country of Carrick and Galloway . From the feudal warlord who had been overthrown at Methven , Bruce was in the process of transforming into one of history ' s great guerilla captains . Bruce had learned well the sharp lesson delivered at Methven : never again would he allow himself to be trapped by a stronger enemy . His greatest weapon was his intimate knowledge of the Scottish countryside , which he used to his advantage time and again . Even at the future battle of Bannockburn , where he temporarily abandoned his guerilla war , he chose his ground with genius , allowing his small army to operate at maximum advantage . As well as making good use of the country ' s natural defences , he made sure that his force was as mobile as possible . Bruce was now fully aware that he could rarely expect to get the better of the English in open battle . His army was often weak in numbers and ill - equipped . It would be best used in small hit - and - run raids , allowing the best use of limited resources . He would keep the initiative and prevent the enemy from bringing his superior strength to bear . Whenever possible crops would be destroyed and livestock removed from the path of the enemy ' s advance , denying him fresh supplies and fodder for the heavy war horses . Most important of all , Bruce recognised the seasonal nature of English invasions , which swept over the country like summer tides , only to withdraw before the onset of winter . Loudoun Hill . Bruce had enemies in all directions but managed to evade them , winning his first small success at Glen Trool , where he ambushed an English cavalry force led by John Mowbray , sweeping down from the steep hillsides and driving them off with heavy losses . He then slipped through the gap in the enemy ring , passing through the moors by Dalmellington to Muirkirk , appearing in the north of Ayrshire in early May , where his army was strengthened by fresh recruits . Here he soon encountered his old enemy , Aymer de Valence , commanding the main English force in the area . In preparing to meet him he took up a position on 10 May at Loudoun Hill , some 10 miles east of Kilmarnock and about 3 miles east of Darvel , both in Ayrshire . With all care Bruce scouted the ground and made the necessary preparations . John Barbour describes his actions in his rhyming chronicle : Valence ' s only approach was over the highway through the bog , where the parallel ditches Bruce ' s men dug outwards from the marsh restricted his room for deployment still further , effectively neutralising his advantage in numbers . He was forced at attack along a narrowly constricted front upwards towards the waiting enemy spears . It was a battle reminiscent in some ways of Stirling Bridge , with the same ' filtering ' effect at work . As Bruce ' s spearmen pressed downhill on the disorganised English knights they fought with such vigour that the rear ranks began to flee in panic . A hundred or more were killed in the battle . Amyer de Valence managed to escape the carnage and fled to the safety of Bothwell Castle . Three days after the Battle of Loudoun Hill Bruce defeated another English force under the Earl of Gloucester . But the greatest boost to his cause came two months later . At Burgh - on - Sands , just short of the Scottish border , Edward I died .