 In 1526 a feud arose with the Clan Kirkpatrick (Kilpatrick).It is recorded in Pitcairn's "Criminal Trials of Scotland" that John Charteris of Amisfield, along with his brother and two sons, were charged with the murder of Roger Kilpatrick, son of Alexander Kilpatrick in March 1526.In 1530 a more notable dispute took place, when Sir Robert Charteris, the eight Laird, fought a duel with Sir James Douglas of Drumlanrig, which has been described as one of the last great chivalric contests.