Rock art carvings (Petroglyphs) have been discovered in adjoining townlands (including Drumirril) dating to 3000 BC.

It is not open to public viewing, A Bronze Age cyst grave was also discovered in Inniskeen Glebe townland.

In this drumlin country, many of the hilltops have hill forts and associated souterrains which date from the late Iron Age or early Christian era.

The country was part of McMahon Clann territory and displaced Carrolls in the 9th century as the dominant force in the area.

Robert Devereux, 2nd Earl of Essex was granted the Barony of Farney, including Inniskeen, by Queen Elizabeth I of England in the late 16th century.

In 1806, the first record of Hurling/Football in Inniskeen as Monaghan beat Louth in a match which is celebrated in the Irish poem Iommain Iniis Chaoin.

More recently, during The Troubles in Northern Ireland, because it is adjacent to Crossmaglen, some people were involved with the Provisional IRA campaign.

Patrick Kavanagh was baptised here, attended regular Mass and served as an altar boy here in his youth.

[7] Kavanagh's universal themes of Soul, Love, Beauty, Nature and God are timeless and will resonate in the hearts of readers of all ages for many generations to come.

[8] In July 2023, Local Link launched route 171 from Shercock to Dundalk, via Carrickmacross and Inniskeen, with several journeys each way daily.

In 2006 Inniskeen won the All-Ireland Intermediate Club Championship by defeating Caherlistrane GAC ar Croke Park.