I've been compiling some from various sources, if you want the full sources, I can add them.
Cunningham Clan in Scotland
The first instance of Cunninghams in written history is when King Malcolm of Scotland, rewarded Malcolm, son of Friskin with the Thanedom of Cunninghame, which is the northern part of Ayrshire, Scotland. The first known Cunningham was Warnebald Cunningham and his son Robertus. Warnebald was granted the lands of Cunninghame by Hugh de Morville in around 1115. Robertus received the lands of Cunningham between the years 1160 and 1180. The Clan Cunningham was well settled in their lands and the parish of Kilmaurs by the late 13th century. The Clan Cunningham fought for King Alexander III of Scotland at the Battle of Largs in 1263. As a result, for this service Hervy de Cunningham, the son of the Laird of Cunningham received a charter from King Alexander III of Scotland confirming all of their lands.
During the Wars of Scottish Independence, the Clan Cunningham supported King Robert the Bruce of Scotland. As a reward for supporting King Robert the Bruce of Scotland the Clan was given the lands of Lamburgton to add to their existing lands. Later during the 14th century Sir William Cunningham of Kilmaurs was one of the Scottish noblemen who were offered to the English as a substitute for the captured King David II of Scotland. His son William married Margaret, the elder daughter and co-heiress of Sir Robert Denniston and through her acquired substantial lands, including Finlaystone in Refrewshire and Glencairn in Dumfriesshire.
In 1421 Henry Cunningham, the third son of William Cunningham, led the Cunninghams at the Battle of Beauge. Sir Williams’s grandson Alexander Cunningham was made Lord Kilmaurs in 1462 and later the first Earl of Glencairn. During the revolt against King James III of Scotland Alexander brought a substantial force to support the King and defeated the rebels at the Battle of Blackness.
In 1488 the Clan Montgomery destroyed the Clan Cunningham's Kerelaw Castle. This was part of a century-long feud that had apparently started when the office of Baillie in Cuninghame, held by the Cunninghams, was awarded to the son of Lord Montgomerie on 31 January 1448-9. Also in 1488 chief Alexander Cunningham, Lord Kilmaurs was killed leading the clan in support of King James III of Scotland at the Battle of Sauchieburn. He was given the title of Earl of Glencairn for his service, but King James IV of Scotland revoked all titles given out by his father and Alexander's son Robert Cunningham was stripped of his title as 2nd Earl of Glencairn.
During the 16th century the long running feud between the Clan Montgomery and the Clan Cunningham continued. Eglington House was burned down and the Montomery chief, 4th Earl of Eglington was killed by the Cunninghams. The government of King James VI of Scotland eventually managed to get the rival chiefs to shake hands.
In 1542 William Cunningham, 4th Earl of Glencairn led the clan against the English at the Battle of Solway Moss where he was captured. He was released for a ransom of £1000. The fifth Earl of Glecairn also called Alexander Cunningham was a Protestant reformer. He was also a patron of the reformer John Knox. In 1556 John Knox performed the first Protestant Reformed Communion service on Easter Sunday under a Yew tree at Finlaystone for the 5th Earl. In 1568 Alexander Cunningham the 5th Earl of Glencairn led the clan at the Battle of Langside near Glasgow.
Cunningham Sept in Ireland
A group of Cunninghams came to Ireland around the 1610 and settled in the very northwest of Ireland, County Donegal, near Derry. There is a story that the migrants were a group of notorious cattle and sheep thieves who were 'persuaded' by their neighbors to leave Ayreshire, Scotland and move to Ireland where their talents could be put to better use. It is more likely that they were brought over from Scotland as part of King James’ orders for the Plantation of Ulster. Land rights to the ‘Grantee’ persons and organizations for huge areas of Irish land confiscated from Irish owners who had participated in military action against English/British interests. The Grantee for 20,000 acres of Land in Donegal County was Ludovic Lennox, the Duke of Lennox, who was not only a Scottish nobleman but also had the good fortune to be a close relative of King James. The land was known as the Precinct of Portlough and was described as being part of the Barony of Raphoe, the regional center at that time.
It was a condition of a Grantee that the land granted must be settled with British farmers and secured against possible repossession by the original Irish inhabitants. The Duke of Lennox looked to his own people in and around Ayrshire in Scotland, the predominant clan in that area being the Cunninghams. He needed ambitious and hardworking individuals and among those that he chose were Sir James Cunningham, who was granted 2,000 acres, John Cunningham, Cuthbert Cunningham and another James Cunningham who was the uncle of Sir James, who each received 1,000 acres. Cuthbert was criticized for his lack of activity in developing his portion but John Cunningham seems to have been active; one account suggests that at one stage he acted as local agent for the Duke. An Alexander Cunningham also received a grant of 1,000 acres further west in another precinct. All these men were from Ayrshire.
James Cunningham’s 2000 acres were in the lands of Machrimore. The area was, and still is, prime farmland close to the shore of Lough Swilly and he was charged with tenanting his lands with loyal settlers, the establishment of a manor, and with organizing the defense of the lands. He brought in landless but capable people from the home area so by 1614 there were 29 tenants on the land and in 1622 over 50 tenants were recorded. He also took over a long abandoned castle, rebuilt it, and added a wall around it to create a place of safety for all in case of attack. This has been referred to as Fort Cunningham and as Castle Cunningham but was not likely to have been put to use as the area was not attacked during the 1641 rebellion. A manor house was built close to the castle and local services established with the arrival of blacksmiths and others. This central settlement lives on today as Manor Cunningham though there seems to be no trace of the original buildings.
John Cunningham’s 1,000 acres were a little to the north along the shore of Lough Swilly in the lands known as Burt. It was he who established NewtownCunningham and named it in keeping with a fashion of the time which saw the establishment of the modern towns of NewtownStewart, NewtownButler and others. There was at one time a permanent garrison at Burt Castle, a local land mark, and of the two settlements this is the one that prospered most in times to come.
In 1629 the settlements were well established and local commerce had started. The king in that year granted ‘patents’ to both places for the right to hold a local market and fairs. ManorCunningham held markets on Thursdays and had two fair days in June and two in October. NewtownCunningham had markets on Mondays and a three day fair starting on St Lukes Day (18th Oct) each year.
The 1659 Census of Ireland
In county Antrim, Barony of Toome, six families named Cunningham (marked “query whither Irish”) were listed. This wasn’t a true census, as it was focused more on surveying men of some social standing in the community.
Principall Irish Names [and] Their Numbers.
Brownes not all Irish; 12; McBride, 9; McCullogh, 5; Cunningham, Query whither Irish, 6; Magrogan, 5; Lorenan, 7; Martin, 7; Mullan, 7; Millar, 7; O Quin, 6; Steill and O Steill, 8.
The English Civil War and Cromwelian Invasion of Ireland
The English Civil War of the mid-1600s pitted the Royalists (the House of Stuart) versus the Parliamentarians, who were lead militarily by Oliver Cromwell. Cromwell was concerned about a Catholic Ireland, so that the Parliamentarians had been determined to retake Ireland, which had been under the control of a Catholic Confederation from about 1641. Oliver Cromwell launched an assault to retake Ireland in 1649. The campaign was brutal, and the resulting war resulted in a death toll of anywhere from 25% to over 50% of the Irish population. In the aftermath, any of the Irish population suspected of ties to the Irish cause were summarily executed; the Roman Catholic religion was banned; and the cry of “To hell or to Connacht" arose – which gave Irish land to Scottish and English settlers and nobility, forcing the Catholic landowners to the Connaught province – dropping Catholic land ownership from 60% to just 8%.
As a number of Cunninghams were expelled from their land in the early 1650s by the Parliamentary forces on the orders of Oliver Cromwell. These were people who had sided with the Royalist cause in the Civil War and had in one way or other given support to the Irish supporters of the Crown. Those Cunninghams that were able to remain in place apparently prospered as their names crop up in accounts of commerce and civic affairs.
Aftwards, the Cunninghams became an influential sept in the area being landowners or substantial tenant farmers. While not a politically powerful group they were regarded as solidly respectable and acceptable in all circles of society. This general acceptability led to the adoption of the Cunningham name by some of the Irish in the area – for example, embers of two well-known Irish Septs in the area, the McCunnigan’s of County Donegal and the Conaghan’s of County Derry took on the Anglicized name of Cunningham. At least by the late 1700’s, there was a process of forced Anglicization across Ireland. All names had to be rendered in English, and both first and last names were therefore Anglicized. It was also part of the Catholic tradition that only names of Saints were accepted at baptism. English was the language for officialdom, but Irish was still the common tongue, so quite often people would use their Anglicized names when dealing with official business, but use Irish and Irish names amongst friends and family. Thus, someone might have been registered John Loughney, but be called Sean O’Lachtna by family. However, John Joseph Cunningham does list English as his native language as well as being the native language of his parents on the US census for 1900, 1910 and 1920.
Battle of the Diamond in County Armagh, Ulster
Family lore said that John Joseph Cunningham, who arrived in Scranton in 1880 at age 16, was from Belfast. He actually wasn’t, nor was his father James Cunningham. However, it is most likely that the grandfather, John Cunningham, born in about 1780 was from Ulster.
In the late 1700, County Armagh in Ulster Province saw repeated factional fighting between Catholics and Protestants, the local population were evenly divided. Beginning in about 1794, the Protestant Peep-o-Day Boys, who were the precursors to the Orangemen, carried out a campaign of ‘wrecking’ Catholic households – essentially breaking into homes, destroying furniture and often setting the house on fire. This culminated in the Battle of the Diamond on September 21st, 1795, between the Catholic Defenders and the Orangemen. The Catholics were mostly unarmed, while the Protestants were organized and well-armed, and were quickly defeated, leaving 20 – 30 of the Catholic Defenders killed. After that, the persecution of Catholics began in full force, with Orangemen posting “To Hell or Connaught” on Catholic homes & cabins. If the family did not leave within a specified time, the house was set ablaze. Within a year, over 7000 Catholics were either killed or left, mostly from County Armagh and County Down.
Approximately 800 families (about 4000 people) were resettled in county Mayo in 1796, and more in the years after, with estimates of 10,000 Catholics ultimately leaving Ulster. Mayo being a predominantly Catholic was generally welcoming of the displaced Catholics. Two families from Drumgor, county Armagh (near Portadown), headed by Edmond Cunningham and John Cunningham left Ulster and settled in the Ballina area. Another, family of four headed by Thomas Cunningham from Edenderry, County Down (next to Belfast), settled in Foxford or Crossmolina.