Battle of Teba The Battle of Teba took place in August 1330 , in the valley below the fortress of Teba , now a town in the province of Málaga in Andalusia , southern Spain . The encounter occurred during the frontier campaign waged between 1327 - 1333 by Alfonso XI of Castile , against Muhammed IV , Sultan of Granada . War on the frontier of Granada . In 1325 , King Alfonso declared war on the Moorish Emirate of Granada and invited other Christian kings to join him in a new crusade . This project came to nothing but Alfonso nevertheless proceeded with a campaign against the western frontier of Granada . In 1327 , he captured the castles of Olvera , Pruna and Torre Alhaquime . In 1330 , a second expedition was mounted to attack the castle of Teba , twenty five miles east of Olvera and a key fortification in the defences of Malaga . Alfonso established his headquarters at Cordoba and sent word to his nobles and knights to concentrate there . A contingent of five hundred knights was also sent by the King of Portugal . By the end of July Alfonso was preparing to march down the Roman road to Ecija where an advance base was to be set up . Scottish knights errant . In 1329 , as Robert the Bruce , King of Scots , lay dying he made one last request of his friend and lieutenant , Sir James Douglas . The King charged that , after his death , Sir James should take his embalmed heart and bear it with him on crusade , thus fulfilling the pledge that Bruce had been unable to honour in his lifetime . The projected campaign in Spain offered Sir James the ideal opportunity . In the spring of 1330 , armed with a safe conduct from Edward III of England and a letter of recommendation to King Alfonso XI of Castile , Douglas set off from Berwick and sailed first to Sluys in Flanders . Here , according to the contemporary Walloon chronicler Jean Le Bel , Douglas ' company consisted of one knight banneret , six ordinary knights and twenty esquires . It is not clear whether the knight banneret was Sir James himself . Other knights named by the Scottish poet John Barbour included Sir William de Keith , Sir William de St . Clair of Rosslyn and the brothers Sir Robert Logan of Restalrig and Sir Walter Logan . Others alleged at one time or another to have accompanied Douglas are John de St . Clair , younger brother of Sir William , Sir Simon Lockhart of Lee , Sir Kenneth Moir , Sir William Borthwick , Sir Alan Cathcart and Sir Robert de Glen but evidence is lacking . There appears to be no historical basis for claims that any of these men were connected with the Order of the Knights Templar , dissolved by Pope Clement V in 1312 , eighteen years previously . Le Bel relates that the Scots party remained at Sluys for twelve days , with Douglas holding court on board ship as if the late king were present . It may be he was awaiting news of the planned crusade and on learning that , despite the withdrawal of his allies , King Alfonso still intended to go to war , he finally set sail for Spain . After a stormy passage , the party arrived at the mouth of the Guadalquivir , probably sometime in late June , and disembarked upstream at Seville . March to Teba . Douglas presented his credentials to Alfonso XI . According to John Barbour , the King offered Douglas riches , fine horses and armour . Sir James declined these gifts , declaring that he and his men were prepared to offer their arms in the service of the king as humble pilgrims , seeking absolution for their sins . Alfonso accepted and assigned experienced soldiers , accustomed to the style of fighting on the " Frontera , " as advisors to Douglas and his fellow knights . While the Scots rested after their long voyage and waited for the expedition to depart , many foreign knights who had come to seek service with Alfonso of Castile paid their respects to Douglas , including a number of Englishmen who were particularly keen to meet the man who until recently had been their nemesis . Alfonso formed up his army for the advance south . Barbour claims that Douglas was given command of the lead division , the ' vaward ' or vanguard . It may be more likely that he was put in charge of all the foreign knights in the Castilian army . The Christian host , its size unknown , marched to Ecija then to Osuna on the frontier . Once across the border , Alfonso continued south to the meadows of Almargen , five miles west of Teba , from where he advanced to set up camp and invest the fortress , While waiting for his siege engine s to come up from Ecija , Alfonso prepared for the Granadan forces in Malaga to react . These were under the command of Uthman bin Abi - l - Ulá , a Berber noble fighting in the service of the sultans of Granada , who set off with six thousand cavalry and an unknown number of infantry to the relief of Teba . Marching up the Guadalhorce valley , Uthman ' s force crossed over into the valley of the river Turón where they pitched camp between the citadel of Ardales and the castle of Turón , ten miles south of Teba . The siege . Meanwhile the siege engines arrived at Teba and operations began to open a breach in the walls of the castle . The Christian army was hampered by a lack of water and they were forced daily to drive their herds out of camp and eastwards down to the Guadalteba , an abundant river flowing two miles south of the castle . Uthman quickly identified this weakness and sent raiding parties to disrupt the watering details . Alfonso in turn set up a defensive screen of patrols to hold them off and there were regular skirmishes on the river and in the hills to the south . It is possible that Sir James Douglas was killed in one of these encounters . The ' Gran Cronica de Alfonso XI ' refers to " " the death of a foreign count through his own error " " , although some commentators prefer to think Douglas died in a more decisive encounter some days later . Alfonso had other problems . The five hundred Portuguese knights declared their term of service was about to expire and withdrew , and one night the garrison of Teba sallied out to attack the siege lines and retired leaving a siege tower in flames . Uthman too faced difficulties . He had concluded he could not defeat the Christians in open battle and so devised a stratagem to force Alfonso to abandon the siege . The battle . Under cover of darkness , three thousand Moorish cavalry prepared to make a diversionary attack across the river while Uthman took another three thousand upstream to make a flank attack on Alfonso ' s camp . At dawn , Uthman ' s river contingent occupied the watering grounds of the Guadalteba . Alfonso , however , having been warned by his scouts of the enemy ' s movements , kept the main force of his army in camp while he sent troops to check the assault developing on the river . Some argue that Douglas and his contingent must have been part of this reinforcement . With battle joined , Uthman believed that his ruse was working and , emerging from the valley where he and his men had been concealed , rode up to attack the Christian camp from the west . When he reached the col overlooking the Almargen valley he saw the camp bristling with Alfonso ' s men armed and ready while at the same time saw his men on the river downstream beginning to fall back . He instantly abandoned the attack and rode back to support his right wing but arrived only in time to join in the general retreat . The Moors on the river had been unable to withstand the weight of the Christian counter - attack . When Alfonso , having seen Uthman ' s move east , sent a further 2 , 000 men to intervene , the Granadan withdrawal turned into a rout . John Barbour , in his description of Douglas ' last battle , describes a similar rout , with Douglas and his contingent pursuing the fleeing enemy closely . There is , however , no mention of the siege of Teba in Barbour ' s account , which describes the Christian army advancing from Seville to repel an invasion from Morocco . According to Barbour , Sir James outruns the rest of his men and finds himself far out in front with only ten or so followers . Too late , he turns back to rejoin the main body . The agile Moorish cavalry see their opportunity , rally and counter - attack . In the running fight that follows , Douglas sees Sir William St . Clair surrounded by a body of Moors , trying to fight his way free . With the few knights still with him , Douglas rides to the rescue but all are killed , including Sir William St . Clair and the brothers Sir Robert and Sir Walter Logan . The Castilian sources do not mention any Moorish counter - attacks during the pursuit , despite the Moors ' notorious capacity for turning on unwary pursuers . Aftermath . The Castilian forces pursued the Moorish army back to their camp in the Turon valley . The chance of a more comprehensive victory was lost when the Christians stopped to loot the enemy tents and baggage . Despite further skirmishes , Uthman made no further attempt to raise the siege and shortly afterwards the garrison of Teba surrendered . The aged Berber general died some weeks later . Barbour tells how Douglas ' body , together with the casket containing the embalmed heart of Bruce , were recovered after the battle . His bones , the flesh boiled off them , and the casket were taken back to Scotland by Douglas ' surviving companions . Douglas was buried at St Bride ' s Kirk , at Douglas , South Lanarkshire . The battle was not decisive . While Teba remained secure in Castilian hands , the Guadalteba and Turon valleys continued debatable land for the next hundred and fifty years . However , in response to Alfonso XI ' s victories of 1327 - 1330 , the Marinid sultan of Morocco Abu Hasan sent forces in support of Muhammad IV to re - establish control of the Straits . Gibraltar was re - captured from the Christians in 1333 but Abu Hasan ' s attempt to re - take Tarifa in 1340 led to his disastrous defeat by allied Christian forces at Rio Salado . This was the last intervention by North African powers in the defence of Muslim Granada .