The Cunninghams of Drumquhassle were a family of the landed gentry in Scotland from the early 16th century to the mid-17th. They are linked to the Cunninghams of Kilmaurs in Ayrshire, being descended through junior lines via the Cunninghams of Polmaise. At their greatest extent, their lands included Mugdock-Mitchell and the house at Killermont (in modern-day Bearsden), covering the part of parishes of Strathblane and New Kilpatrick. John Cunningham, the third laird held several positions of responsibility within the Scottish court, including Master of the Royal Household for James VI and a Collector General of tax during the regency of the Earl of Lennox, but his involvement in the power struggles between the Scottish nobility and the court of Elizabeth I of England also led to his demise and he was executed for treason in 1585. Over the next century, the family lost its land and power – in the mid-17th century, the Cunninghams sold their country house in Drumquhassle in rural Stirlingshire and it passed to the Govane family.
The Cunninghams of Drumquhassle (alternative spellings include Drumwhassle and Drumquhassill, meaning ridge with the castle (a Roman fort was built there) ) were descended from one of the younger sons of Sir Robert Cunningham of Kilmaurs, and then through one of the younger sons of Andrew CunninghamNote 1 of Polmaise, named Alexander. This Alexander Cunningham (first Laird of Drumquhassle) married Margaret Park (about 1502), and in this way acquired three quarters of the lands of Mugdock (the remainder, including the castle, was in the hands of the Clan Graham)). Alexander's son and heir, Andrew, married Mary, the daughter of Robert Erskine, 4th Lord Erskine, and their son John became the third Laird prior to July 1548. John married Isobel Cunningham (Janet, according to some records) a relative and co-heiress of the Polmaise estate. On 27 May 1556, her sisters (Margaret and Katherine) sold their parts of Polmaise to John and Isobelle. It was under the third laird that Drumquhassle was made a barony, with Drumquhassle Castle as its principal seat.