Enniskillen Castle was besieged numerous times by Irish, English, and combined forces of Irish and English.

Here is a timeline of the attacks on Enniskillen Castle:

1508 - Hugh O'Donnell attacks with a fleet of boats - takes the castle from Rory Maguire and gives it to Philip Maguire.

1508 - Hugh O' Donnell returns and burns castle to the ground.

1538 - Castle destroyed again this time by O'Neill with a party of English and ordnance.

1594 - The English under Captain Dowdall is besieged by land and they take it by water.

1595 - In the month of May the castle is besieged and taken back by Maguire.

1595 - In the month of September, besieged by the English under Sir William Russell.

1596 - Maguire recaptures castle.

1602 - Cuchonnacht raised the castle to prevent English using it as a base.

1602 - Niall Garbh O'Donnell and a force of English complete the destruction of the castle.

One of the best documented assaults on Enniskillen castle took place in 1594. The castle was besieged and eventually captured by the English under Captain John Dowdall, but was recaptured by Hugh Maguire shortly afterwards.

Later in the year the Lord Deputy, Sir William Russell, led the English in another successful capture of the castle but in the following May Hugh Maguire again won back his castle.