The Douglas family built the first Douglas Castle, which was constructed of either wood or stone, sometime before 1288. In 1307, during the Wars of Scottish Independence the castle was captured and garrisoned by the English under Lord Clifford. Sir James Douglas, companion of Robert the Bruce successfully recaptured his family seat by storming the castle on Palm Sunday, while the garrison were at chapel. he had the garrison killed and thrown into a cellar, before the structure was burned.
The event has become known as "Douglas' larder".
Robert the Bruce rewarded the loyalty of the Douglases, and Sir James' heirs were created Earls of Douglas. Douglas Castle was rebuilt as one of their strongholds, but by the 15th century, the power of the "Black" Douglases had come to threaten the Stewart monarchy. In 1455 James II led an expedition against the rebellious 9th Earl, defeating his forces at the battle of Arkinholm. Douglas Castle was sacked and the family's lands and titles forfeited.
The "Red" Douglases, Earls of Angus, had sided with the king against the senior branch of their family, and it was they who gained the Douglas lands in Lanarkshire. It is likely that the castle was rebuilt soon after 1455. Regent Morton came to Douglasdale in June 1574 to survey the house of the Earl of Angus with a view to repairing it and living there.
In 1703, Archibald Douglas, 3rd Marquess of Douglas was created Duke of Douglas, with his principal seat at Douglas Castle. The castle was again rebuilt around this time, as a tower house and an enclosed courtyard with a corner tower. This castle was destroyed by fire in 1755, with the exception of the corner tower.