In the late 1390s, a series of events occurred that began to push Owain towards rebellion, in what was later to be called the Welsh Revolt, the Glyndŵr Rising or the Last War of Independence.

Campaigns conducted from the Haven included part of Henry II's Invasion of Ireland in 1171 and Cromwell's own attack on Ireland in 1649, while forces which have disembarked at the point include Jean II de Rieux's 1405 reinforcement of the Glyndŵr Rising.

It was used as the base for several military operations, such as Henry II's Invasion of Ireland in 1171, and Oliver Cromwell's 1649 invasion of Ireland ; while forces which have disembarked at the point include Jean II de Rieux's 1405 reinforcement of the Glyndŵr Rising and Henry VII's 1485 landing at the waterway before marching on England.

There was a resurgence of interest in Clun Castle during the Glyndŵr Rising of 1400 – 15, with Thomas playing a key role in suppressing the revolt ; the castle was refortified and saw some service against the Welsh rebels led by Owain Glyndŵr.

It was part of the Glyndŵr Rising or Welsh Revolt of 1400-1415.

Owain Glyndŵr (), or Owain Glyn Dŵr, ( c. 1349 or 1359 – c. 1416 ) was a Welsh ruler and the last native Welshman to hold the title Prince of Wales.

Glyndŵr has remained a notable figure in the popular culture of both Wales and England, portrayed in William Shakespeare's play Henry IV, Part 1 ( anglicised as Owen Glendower ) as a wild and exotic man ruled by magic and emotion (" at my nativity, The front of heaven was full of fiery shapes, Of burning cressets, and at my birth The frame and huge foundation of the earth Shaked like a coward.

In 2000, celebrations were held all over Wales to commemorate the 600th anniversary of the Glyndŵr rising.

Glyndŵr was born circa 1354 ( possibly 1359 ) to a prosperous landed family, part of the Anglo-Welsh gentry of the Welsh Marches ( the border between England and Wales ) in northeast Wales.

Upon the death of his father-in-law, Sir David Hanmer, in late 1387, knighted earlier that very year by Richard II, Glyndŵr returned to Wales as executor of his estate.

For example, during the 1980s, a group calling themselves " Meibion Glyndŵr " claimed responsibility for the burning of English holiday homes in Wales.

A statue of Owain Glyndŵr on horseback was installed in 2007 in The Square in Corwen, Denbighshire to commemorate his life and his lasting influence on Wales.

In 2008, Glyndŵr University was established in Wrexham, Wales.

* BBC Wales History-Profile of Owain Glyndŵr

* 1400 – Owain Glyndŵr is declared Prince of Wales by his followers.

* probable – Owain Glyndŵr, last Welsh Prince of Wales ( d. 1416 )

* September 16 – Owain Glyndŵr is proclaimed Prince of Wales by his followers and begins attacking English strongholds in north-east Wales.

* June 14 – Rebel leader Owain Glyndŵr, having declared himself Prince of Wales, allies with the French against the English.

* September – Henry, Prince of Wales ( later Henry V of England ) retakes Aberystwyth from Owain Glyndŵr.

Less than three years later, Henry was in command of part of the English forces — he led his own army into Wales against Owain Glyndŵr and joined forces with his father to fight Harry Hotspur at Shrewsbury in 1403.

Rebellions continued throughout the first ten years of Henry's reign, including the revolt of Owain Glyndŵr, who declared himself Prince of Wales in 1400, and the rebellion of Henry Percy, 1st Earl of Northumberland.

By 1400 Owain Glyndŵr had begun a rebellion in Wales.

They subsequently supported him in Wales, early in the rebellion of Owain Glyndŵr, and in Scotland, in both negotiations and conflict against the Scots.

It appears that he may have hoped to be reinforced by a Welsh force under the self-proclaimed Prince of Wales, Owain Glyndŵr.

In 1400 a revolt broke out in North Wales against English rule, led by Owain Glyndŵr.

In 1400 a revolt broke out in North Wales against English rule, led by Owain Glyndŵr.

On 16 September 1400, Glyndŵr instigated the Welsh Revolt against the rule of Henry IV of England.

In 1400, Lord Grey informed Glyndŵr too late of a royal command to levy feudal troops for Scottish border service, thus being able to call the Welshman a traitor in London court circles.

In 1400, a Welsh nobleman, Owain Glyndŵr ( or Owen Glendower ), revolted against King Henry IV of England.

Damage was done to the church in 1400 during the rebellion of Owain Glyndŵr ; his forces also destroyed the Bishop's Palace at Llandaff.

Ranulf Higden in his Polychronicus records the Flemings as extinct in Pembrokeshire by 1327 but Flemish mercenaries reappear in 1400 when at the behest of Henry IV they joined an army of 1500 English settlers who marched north from Pembrokeshire to attack the army of Owain Glyndŵr at Mynydd Hyddgen.

Henry Bolingbroke took the English throne to rule as Henry IV in 1400, but rebellion broke out in North Wales shortly afterwards under the leadership of Owain Glyndŵr.

Later, Oswestry was attacked by the forces of Welsh rebel leader Owain Glyndŵr during the early years of his rebellion against the English King Henry IV in 1400 ; it became known as Pentrepoeth or ' hot town ' as it was burned and nearly totally destroyed by the Welsh.

In 1400 the Welsh prince Owain Glyndŵr rose in rebellion against English rule, and in response in 1404 100 marks was spent by the royal government improving the fortifications to protect Brecon in the event of a Welsh attack.

Owain Glyndŵr unsuccessfully assaulted it at the commencement of his revolt in 1400.

The next few years Fitzalan was much occupied by events in the Welsh marches, where he had to help deal with the revolt of Owain Glyndŵr which ran in full from 1400 to maybe 1412 but gained a great deal of early momentum until 1405.

A final rebellion in 1400 led by Owain Glyndŵr, a member of the rival royal house of Powys, also drew considerable support from within Gwynedd.

The town was devastated by the forces of Owain Glyndŵr in 1400 at the start of his rebellion against the English king Henry IV.

Henry had already declared Owain Glyndŵr, a descendant of the Princes of Powys, a traitor, and on 16 September 1400 Owain launched a revolt.

The castle was said to have been attacked and destroyed by Owain Glyndŵr and his forces during his rebellion of 1400 to 1412.

Denbigh was also burnt in 1400 during the revolt of Owain Glyndŵr.

The castle was refortified on the Royal command of new King King Henry IV in 1400 and carried out by Sir John Pauncefote, great grandson of Sir Grimbold, in advance of the uprising led by Owain Glyndŵr to 1412.

The palace was burnt down by Owain Glyndŵr in 1400 and the ruins have mostly been washed away together with much of the township by coastal erosion in the Conwy Estuary.

The Lordship of Gwyddelwern was a junior title within the House of Powys Fadog and was recorded in 1400 as being held by Tudur ab Gruffydd Fychan II who was the younger brother of Owain Glyndŵr.