In February 1594, the English had captured Enniskillen Castle from the Irish after a waterborne assault and massacred the defenders after they surrendered.

In 1593, Hugh Maguire, Chief of the Name and Lord of Fermanagh, had objected to the behaviour of the newly-appointed English Crown sheriff Humphrey Willis.

As he had done before being expelled by Hugh Roe O'Donnell from Tyrconnell in 1592, Willis was cattle raiding and plundering throughout Clan Maguire territory.

In May and June 1593, Maguire and Brian Oge O'Rourke of West Breifne raided lands held by the English Lord President of Connaught, Richard Bingham.

[1] Captain Thomas Lee, who was present, described this as a great dishonor to the Queen as the defenders had surrendered "uppon composicion, And your majesties worde being past to the poore beggars that kept it, they were all notwithstandinge dishonourably putt to the sworde in a most miserable state".

[4] On 17 May 1594, now acting with the covert support of Tyrone, Hugh Maguire and Cormac MacBaron O'Neill laid siege to Enniskillen which was now isolated in hostile country.

Many of the garrison fell sick due to food shortages and exhaustion brought on by incessant skirmishing with the Irish.

This time, forty picked men dressed in chain mail and armed with Lochaber axes attacked at night.

This was inconsistent with the treatment of other English garrisons, such as the Blackwater Fort, who were granted liberal terms to leave their position in February 1595.

However, the Enniskillen garrison may also have been slain as retaliation for Dowdall's similar violation of the surrender terms and massacre of Clan Maguire's defenders of the castle and their families in the year before.