Killywilly is a townland in the civil parish of Drumlane, Barony of Loughtee Lower, County Cavan, Ireland.
The earliest surviving mention of the townland is on the 1609 Ulster Plantation map of the Barony of Loughtee, where it is spelled Killivelly.
An Ulster Plantation grant of the 'Manor of Monaghan', dated 21 June 1610, from King James VI and I to Sir Hugh Wyrral, a native of Enfield, Essex, England, included one poll of Keilenolin.
[7] Bagshaw's daughter, Anne, married Thomas Richardson of Dublin, son of John Richardson, bishop of Ardagh, and the marriage settlement dated 28 May 1654 transferred the estate to the married couple.
On 30 April 1661 the Richardsons sold part of the estate, including one & a half polls of Killewooley which included a subdivision called 'Tenorerine' (perhaps an Anglicisation of the Irish "Tamnach Rinn", meaning 'The Pasture of the Headland'), to Captain Ambrose Bedell of Carn, Tullyhunco, County Cavan.