Perhaps more than any other castle, Stirling represented Scotland's military resistance to English aggression in the Middle Ages. In the War of Independence it was constantly being attacked, its buildings destroyed and then rebuilt. In 1296, it was seized by Edward I of England. A year later, Wallace recovered it but lost it again in 1298. In 1299, the Scots took it again and held it until 1304, the year of the great siege by Edward I which was planned with some cart. For three months the garrison resisted everything the old warrior could hurl against it, including a battery of siege-engines weighted down with lead stripped from neighboring church roofs, under the general control of Master James of St George. These engines hurled Greek fire, stone balls and possibly even some sort of gunpowder mixture  At the end of July the garrison surrendered. The English held the castle for ten years, but in 1314 it was yielded to the Scots after their great victory nearby at Bannockburn, and it was then dismantled.
The structure that endured so much battering had begun as a timber and earthwork castle tailored to the great basalt rock some 76 metres (250 ft) high at Stirling, which commanded the main route into the Highlands. Alexander I (1107?24) built a chapel, and died there. David I stayed there on many occasions and his grandson, William the Lion, died there in 1214. But of the buildings of these years nothing remains. The complex of stone structures and walls that graces the huge rock today stem from the fifteenth century and later.

Stirling became a more permanent Crown residence under the Stewarts. The oldest surviving stone buildings, although doubtless not the first to be erected, are the gatehouse with its square centre block containing the entrance passage, and two narrower side entrances. The block is flanked by the great hall and also by substantial cylindrical towers which once had roof caps but which were replaced in the eighteenth century by crenellations.

The great hall was designed and built by Robert Cochrane, favorite of James III (1460-88), and it was one of the first and certainly the finest of the fifteenth-century Renaissance buildings erected anywhere in the British Isles. James IV began the great Palace Block with its rich carving on the north and south faces, and this was continued by his son, James V. In c.1594, James VI rebuilt a much earlier chapel, probably of c.1470-80.
James, the infant son of Mary, Queen of Scots, was baptised in Stirling in 1566, and a few months later he was crowned there as James VI, aged only 13 months, when his mother was forced to abdicate. Stirling's last military experience was an attack by Bonnie Prince Charlie in 1745