During the Anglo-Scottish war of the Rough Wooing, in December 1547 he sailed two ships to Dundee to support the English garrison at Broughty Castle commanded by Sir John Luttrell.
During the Anglo-Scottish war of the Rough Wooing, Wyndham commanded a ship at the landing at Edinburgh in 1544. In December 1547 he sailed two ships to Dundee to support the English garrison at Broughty Castle commanded by his relation Sir John Luttrell.