The McCullochs first emerge into documented Scottish history with the mention of three men of that name in the Ragman Roll of 1296. When King Edward I of England briefly conquered Scotland, he made a record of all Scottish chiefs and nobles and had them apply their seals to the Roll. This historic document is now in the Tower of London Archives. Thomas Mackulagh, the Count Wiggetone, was the first Gallovidian Scot to apply his seal rendering homage to Edward. By 1305, Thomas was the powerful Sheriff of Wigtown. Also signing the roll were the chieftain brothers of Michael and William Mackulagh. All three were prominent supporters of the powerful Balliol faction which was opposed to Robert the Bruce. When Robert the Bruce gained Galloway for the Scottish Crown, the Balliols and their McCulloch supporters were driven out. There is no reason however to term these McCullochs as traitors to their country as John Balliol's mother, Devorguilla, was a daughter of Alan, the last hereditary Lord of Galloway. It was only to be expected that Gallovidian families should support the Balliol cause, and when Balliol submitted to the English King, his followers, of course, did likewise.

In 1353, the McCullochs swore allegiance to King David II of Scotland and in 1360, Patrick McCullagh received compensation of 100 merks for his family's sufferings and loss of lands in Scotland during their staunch support of the Balliols and the King of England. Three years later, in 1363, Patrick's son, Sir Patrick McCulloch, had the family's Scottish lands restored to him by King David II of Scotland, a final sign that the family had regained the King's trust and favour.

From 1363 to 1463, documentary evidence is scant on the Gallovidian McCullochs and it is during this period that some cadet branches of the family may have moved north to the Highlands through marriage or after serving as mercenaries abroad. Certainly about 1368, John MacCulloch of Tarrell appears in the records of Rosshire, most local histories merely stating that the MacCullochs, who were not indigenous to the region, "may have come into Easter Ross from some other part of Scotland." In 1458, John, Earl of Ross, Lord of the Isles, and Sherriff of Innernys (Inverness) addressed to John MacCulloch, Bailie [Bailiff}] of the girth of Sanct Duthowis, a letter requiring him "to protect the privileges of Innernys in that quarter." The Scottish Antiquary (1898) relates that "among the aristocracy of the earldom of Ross there was no name more respected than that of MacCulloch, whose original designation was of Plaidis." Several generations were so designated, until John MacCulloch, Provost of Tain, in 1621 changed his style to that of Kindeace...

In The Roll of Clannis of 1387, the McCullochs were listed as a Border Clan and although the McCulloch territories were never adjacent to the English border, they were part of Scotland's coastal defence. It was estimated at this time that the McCullochs could put more than 500 warriors into the saddle to police the coastline and protect their own territories. Raiders from Ireland, Wales and the Isle of Man were commonplace, not to mention those of the local variety who propagated the internecine squabbles of the border clans themselves.

The link between Galloway and Rosshire, lowland to highland, may be through the most illustrious of the old McCullochs who lived in the late 1400's and early 1500s. Sir Alexander McCulloch of Myretoun, also known in local legend as Cutlar McCulloch, Walter Jameson McCulloch relates in his History of the Galloway Families of McCulloch, that Sir Alexander was "for the greater part of his life...in close, even intimate, touch with the royal circle." He married Marjorie, the daughter of the 2nd Lord Sinclair, and grandaughter of the Earl of Rothes in Moray on her mother's side. Sir Alex was no stranger to the Orkneys and Shetlands as he travelled there on the king's business to purchase falcons, no doubt passing through Rosshire on his travels. Of Sir Alexander's father, Eliseus, and grandfather, Normand, very little is known but they may also have established earlier ties to the Earl of Ross through marriage. Certainly the Argyllshire McCullochs were linked to Angus, the Earl of Moray, neighbour to the Earl of Rothes. The MacLullichs supposedly descended from the Earl of Moray and these supporters of the Clan Donald may have supported Donald of the Isles, a grandson of Robert II, who fought for the Earldom of Ross in right of his wife, a member of a lowland family, early in the 15th century. Donald suffered defeat at the hands of the Fraser and MacKays at Harlaw.

Other Argyllshire MacCullochs hail from the neighbourhood of Oban and the island of Kerrara. MacCulloch of Colgin, near Oban was regarded as the head of the Argyllshire McCullochs.

In 1466 Gilbert McCulloch witnessed a charter, and it was probably he or his son, James McCulloch of Cardoness who built Cardoness Castle, a fine example of early Scottish architecture, particularly for its display of interior decorative detail. Overlooking the River Fleet estuary, it would be the principal McCulloch stronghold for over 200 hundred years. Other smaller tower keeps were built at Myretoun and Barholm.

James contrived to gain control of the neighbouring MacLellan lands by having his only daughter marry Alexander MacLellan. He died in 1500 and was succeeded by Ninian, who despite being sheriff deputy was prosecuted for stealing 1500 beasts from a barn and for illegally collecting rents, which should have went to his mother. Ninian died, or was executed for his crimes, in 1509. His heir, Thomas, was a minor. The MacLellands seized Cardoness. Thomas was succeeded by his brother, Alexander, in 1516. He is known to have carried out a series of raids on the Isle of Man in the 1530s which gave rise to the Man proverb;

The constant feuding between the McCullochs and their neighbours was to bring about their financial ruin. In 1592 they were forced to mortgage the estate. They lost it in 1628 to John Gordon of Upper Ardwall, one of families they were so often at odds with. The family of McCulloch of Myretoun was raised to the rank of baronet of Nova Scotia by Charles I in 1634.

It is not clear whether the Gordons allowed them to stay on in the castle but by 1668, they were back. Alexander McCulloch, Keeper of Falcons to James IV, was heavily fined for assaulting John Gordon's widow. He is said to have dragged her from her sick bed, out of the house, and threw her on to a dung heap.

His son, the last baronet, Sir Godfrey McCulloch, shot and killed Gordon himself at their house at Bush o'Bield, a crime for which he received the death penalty. He escaped and fled overseas for some time but, he made the mistake of coming back. He was spotted attending a service at St. Giles in Edinburgh. His one claim to fame in the Scottish history books is that he was the last man to be ever executed on The Maiden - the Scottish equivalent of the guillotine.