The family Cunningham take their name from the district of Cunningham in northern Ayrshire. The land of Kilmaurs of that area was granted by Hugo de Moreville, Constable of Scotland to a vassel named Warnebald in the 12th century and it is from his descendants that the Cunningham family originate.

Harvey de Cunningham of Kilmaurs was amoung those who fought against the King of Norway at the Battle of Largs in 1263 and for his bravery his possession of Kilmaurs was confirmed by Alexander II. Robert the Bruce granted further lands and through the marriage of Sir William Cunningham to Margaret, daughter of Sir Robert Dennieston the Cunninghams extended their possessions further to include Glencairn. His grandson Sir Alexander de Cunningham was created Lord Kilmaurs in 1462 and then Earl of Glencairn in 1488 by James III. However he died with James at the Battle of Sauchieburn in that year.

William, 3rd Earl was captured at Solway Moss but released in exchange for support of the marriage of Mary Queen of Scots to King Edward VI of England. Alexander, 5th Earl of Glencairn was a supporter of the Reformation and responsible for the destruction of the chapel at Holyrood, his Protestant sentiments fuelled the longstanding feud between the Cunninghams and the Montgomeries, Earls of Eglinton. However the 9th Earl returned to the Stewart side leading the rising of 1653 for Charles II. The rebellion was defeated but he was made Lord Chancellor after the Restoration in 1660. The 14th Earl, John was a friend of Burns and on his death in 1791 Burns wrote "Lament for the Earl of Glencairn".