 In 561 AD the Battle of Cúl Dreimhne (also called the Battle of the Book) was fought at Cooladrumman, a townland near Drumcliff in this territory.This territory, under the shadow of Benbulbin (from the ), is where Conall Gulbain set out to conquer Tír Chonaill, modern Donegal.Cairbre Drom Cliabh remained closely associated politically with the Cenel Conaill but pressure from the Kingdom of Breifne continued and various kings were imposed by them