The early history of Clan Middleton is described in detail in the 17th century work of Frederic van Bossen, who claimed that the first Lord of Middleton was Freskin, the brother of Kenneth de Cunninghame; and the son of Kenneth and Lady Sponsa, who was the sister of Albinack ap Crinain.

[6] In 1296, Humfrey de Middleton of Kincardyn appeared on the Ragman Rolls rendering homage to Edward I of England.

[6] Middleton was with David Leslie, 1st Lord Newark's cavalry when they surprised and defeated James Graham, 1st Marquess of Montrose at the Battle of Philiphaugh in 1645, pursuing him northwards.

[6] He was tried for treason, but again escaped and joined Glencairn's rising, only to be defeated by George Monck, 1st Duke of Albemarle, and went into exile again on the Continent.

[6] Charles did not approve of the actions of James II of England and VII of Scotland, but did not support the Glorious Revolution of 1688 or the subsequent ascension of Queen Mary and William of Orange, fleeing to France.

[6] Sir Thomas Middleton of Rosefarm was a distinguished agriculturalist and deputy director general of the Department of Food Production during World War I.