The second siege of Enniskillen begins on May 17, 1594.

The siege of Enniskillen takes place at Enniskillen in Fermanagh, in present day Northern Ireland, in 1594 and 1595, during the Nine Years’ War. In February 1594, the English capture Enniskillen Castle from the Irish following a waterborne assault and massacre the defenders after they surrender. From May 1594, an Irish army under Hugh Maguire and Cormac MacBaron O’Neill besiege the English garrison in the castle, and in August they defeat an English relief force in the Battle of the Ford of the Biscuits. A second relief force is allowed to resupply the garrison, but the castle remains cut off. Eventually, in May 1595, the English garrison surrenders to the Irish and are then massacred.

Enniskillen Castle sits on the River Erne and commands the strategic bottleneck between Upper and Lower Lough Erne. On January 25, 1594, English Captain John Dowdall arrives at Enniskillen by boat with three infantry companies. They dig trenches in which they place light cannons and musketeers, but the cannons are too small to make much of an impact on the castle walls. On January 30, Captain George Bingham arrives with 300 men.

They launch a waterborne assault on the castle. While musketeers in boats and artillery on land fire at the castle, a large boat holding 67 men anchors at a vulnerable part of the walls. They make a breach in the wall with pickaxes, forcing the Irish to take shelter in the keep. Dowdall threatens to destroy the castle with gunpowder if the garrison does not surrender. An Irish witness claims there are 36 fighting men and 40 women and children in the castle, while Dowdall claims there are 200. After they surrender, Dowdall has them put to the sword and claims to have killed 150. Captain Thomas Lee, who is present, describes 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.”

Dowdall writes on February 2 to the Lord Deputy of Ireland that he has captured the castle from the “rebel” Hugh Maguire. An English garrison is left in place. A detailed coloured illustration of the siege is made shortly after.

On May 17, 1594, now acting with the covert support of Hugh O’Neill, Earl of Tyrone, Hugh Maguire and Cormac MacBaron O’Neill lay siege to Enniskillen which is now isolated in hostile country. Their army consists of 1,400 foot soldiers and 600 horsemen. It quickly grows with support arriving from Hugh Roe O’Donnell. The English commander, James Eccarsall, has only 50 foot soldiers and 24 horsemen to defend the castle, along with some light artillery. Eccarsall launches a sortie by boat but has to retreat under heavy fire. Irish fortifications cut off access by river and the castle is attacked nightly. Many of the garrison fall sick due to food shortages and exhaustion brought on by incessant skirmishing with the Irish.

On August 7, Maguire and his allies defeat an English relief force for Enniskillen at the Battle of the Ford of the Biscuits. A second relief force commanded by the Lord Deputy of Ireland, William Russell, is sent by another route. Although it is not attacked by the Irish, none of Russell’s scouts or messengers reach the castle nor return. Russell relieves the beleaguered garrison by August 30 with six months supplies, then withdraws. Following this, there is a truce, but “subterfuge and deception were the hallmarks of this stage of the war.”

Maguire raises the clan and the castle is again attacked in January 1595 (Third Siege of Enniskillen). This time, forty selected men dressed in chain mail and armed with Lochaber axes attack at night. His men overrun the outer defences but the garrison holds out in the tower. The Irish withdraw but take with them the garrison’s three boats, preventing the English from patrolling the Erne and cutting them off.

The garrison’s plight is not lost on the authorities in Dublin, but the Crown does not have enough troops for a relief force, and Lord Deputy Russell considers withdrawing the garrison. A report to the Lord Deputy of Ireland suggests that Clan Maguire plans to bring down the walls with gunpowder. In May 1595, the garrison agrees to surrender Enniskillen to the Irish in exchange for their lives. However, the entire garrison is then massacred. Russell claims that the garrison had surrendered on terms to Cormac MacBaron O’Neill, who then reneged upon his word and had the surrendered garrison executed en masse. This is inconsistent with the treatment of other English garrisons, such as the Blackwater Fort, who are 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.