In 1306, Scottish forces led by Robert Wishart, Bishop of Glasgow, attacked the English garrison at the castle and besieged it.

Wishart was captured by the English at Cupar and imprisoned until he was ransomed after the Scottish victory at the Battle of Bannockburn.

In 1308 the Warden of Cupar Castle, Sir Thomas Grey, was ambushed on his way back from Edward II's coronation by a follower of Robert Bruce, Walter de Bickerton.

[2] Although heavily outnumbered, Thomas routed Bickerton's men through the use of cavalry charges and by deceiving his enemy that they were greater in number than they really were.

In April 1336 the forces of Robert Stewart, then Guardian of the Realm laid siege to Cupar Castle.