| 1109 | | Abduction of Princess Nest
|
| | Nest, the wife of Gerald de Windsor, was abducted along with her children possibly from Cilgerrran Castle. She was abducted by one of her own relatives, Owain ap Cadwgan. |
| 1136 | | Battle of Crug Mawr
|
| | The Normans were defeated in battle at Crug Mawr, south west Wales, by a Welsh army. Cilgerran Castle then fell to the Welsh. |
| 1204 | | William Marshall captures Cilgerran
|
| | William Marshall captured the Welsh castle at Cilgerran in Pembrokeshire from the Welsh. |
| 1215 | | Llewellyn captures Cilgerran Castle
|
| | Llewellyn's fight against the Normans continued with the capture of Cilgerran Castle. |
| 1223 | | Cilgerran Castle recaptured
|
| | William Marshall, the younger, recaptured the castle at Cilgerran from Llewelyn ap Iorwerth. |