The Battle of Drumderry was fought between a band of Irish tóraidhe brigands and Seamus Hennessey's party of Irish Confederate irregulars on 30 September 1642 amid the Irish Confederate Wars.
After his escape from Parliamentarian captivity following the Battle of Kilmurry, Hennessey raised a new band of followers in County Tipperary, insisting on continuing his resistance against the Anglo-Irish of County Cork until they were driven out. Along the way, his party was ambushed by a force of tóraidhe brigands, but his men charged the poorly-armored brigands and massacred them. The loot taken from the brigands helped fund Hennessey's raising of a larger army.