Henry IV
Henry IV
 16 September 1400
 18 - 23 September 1400
 24 September 1400
 End of September 1400
 28 September 1400
 8 October 1400
 15 October 1400
  October 1400
  Winter 1400
  March 1401
  Early April 1401
  April 1401
  April 1401
  May 1401
  May 1401
  May 1401
  June 1401
  June 1401
 mid to late June 1401Pumlumon uplands
the Pumlumon Uplands
  July 1401
  Autumn 1401
harlech castle
  Early October 1401
  October 1401
military preparations
  October 1401
military preparations
  Late 1401
  Early November 1401
  November 1401
  January 1402
military preparations
  January 1402
  March 1402
military preparations
  April 1402
  May 1402
military preparations
 22 June 1402
  July 1402
military preparations
military preparations
  July 1402
 26 July 1402
military preparations
  August 1402
harlech castle
 14 September 1402
 30 November 1402
  Early 1403
  January 1403
 22 February 1403
hope burns
hope burns
 1 April 1403
military preparations
  May 1403
  May / June 1403
 24 June 1403
military preparations
  July 1403
 10 July 1403
 11 July 1403
 21 July 1403
  August 1403
 13 August 1403
  August 1403
  September 1403
  October 1403
  October 1403
military preparations
  October 1403
military preparations
  November 1403
  November / December 1403
  January 1404
  Early 1404
  January - February 1404
  Early 1404
military preparations
  Spring - summer 1404
villages burn
villages burn
  March 1404
 1st? May? 1404
machynlleth parliament
  May 1404
  July 1404
 20 August 1404
  August 1404
  Summer 1404
  Summer 1404
  April 1405
military preparations
  May 1405
  June 1405
  June 1405
  July 1405
  August 1405
  August 1405
  August 1405
machynlleth parliament
  September 1405
  September 1405
  Early 1406
 12 January 1406
  January 1406
 1 February 1406
  February 1406
military preparations
  March 1406
  March 1406
  March 1406
 23 April 1406
  Spring 1406
  June 1406
 20 August 1406
  Summer 1406
military preparations
  September 1406
  from October 1406
 9 November 1406
 18 November 1406
  December 1406
  Early 1407
military preparations
  late March / early April 1407
  May 1407
military preparations
 1 June 1407
  May / June 1407
  May / June 1407
  August to November 1407
military preparations
  August to November 1407
military preparations
  November 1407
 19 February 1408
  May 1408
  May 1408
  Spring 1412



Richard II is overthrown by Henry Bolingbroke. A move that is not generally supported by the Welsh aristocracy

Crowned Prince

Owain Glyndwr proclaimed Prince of Wales


Owain Glyndwrs supporters (Plant Owain, the children of Owain) attack Ruthin, Denbigh, Rhuddlan, Flint (where they attacked the English relieving force), Holt, Oswestry and Welshpool


Outside Welshpool and the banks of the Vyrnwy an English force led by Hugh Burnell scatters the Welsh forces.

1st Expedition

Henry IV's army diverted to Shrewbury on its way back from Scotland. It commences campaigning in North Wales

Heads Roll

8 rebels executed

Estates forfeited

Owain Glyndwr and other leading rebels are officially outlawed. Glyndwrs estates are confiscated and granted to John Beaufort Earl of Somerset


Henry IV's army returns to Shrewbury

Scale Down

English relief force is disbanded and the Flint garrison scaled down

A winters tale

Owain Glyndwr and his men have withdrawn to Snowdonia near Llyn Peris

Pardon offered

Henry IV offers to pardon all rebels except for Owain Glyndwr

Find Glyndwr!

Spies are sent to Merionethshire, Llyn, Eifionydd to find Glyndwr

Judicial Sessions

Hotspurs judicial sessions allocate subsidies of 1000 marks to the communities of Caernarfonshire and Merionethshire

Conwy Captured

Rhys ap Tudur and Gwilym ap Tudur capture Conwy Castle (to secure a pardon?)

Set backs...

A band of Glyndwr's men are routed by Hotspur near Cader Idris then scattered by John Charlton Lord of Powys

Moving, keep on moving...

Glyndwr moves his base of operations south to the Pumlumon uplands, just south of Machynlleth

General Contagion

Robbers & malefactors in Brecon / Rebellious villeins in Abergavenny / Rebels in Powys / Assemblies of rebels in Carmarthenshire

Conwy Returned

Conway Castle handed back...after negotiation with Hotspur


Spies are sent to the uplands of Nant Conwy and Traeth Mawr

The Battle of Hyddgen

An anglo-flemish force of some 1500 men is raised in Pembrokeshire and the surrounding areas and attacks Owain Glyndwr and his men on Mynydd Hyddgen. Owain and his 500 or so men are taken by surprise and surrounded,. Following lengthy fighting, Owain and his men attempt to break out taking the attackers by surprise. The attackers take flight and leave behind 200 of their own dead - Glyndwr is victorious!


Rhys ap Tudur and Gwilym ap Tudur are pardoned - their co-conspirators are executed

Men of Harlech

Harlech laid seige -- relief force sent from Chester

2nd Expedition

Henry IV's 2nd expedition sets out to the Tywi valley and Strata Florida

Yes Lieutenant

The Earl of Worcester is appointed Lieutenant of South Wales


Castles are garrisoned -- especially Aberystwyth and Cardigan

Islands of calm in a sea of rebellion

Amidst the mounting chaos Flintshire and lowland South Wales are relatively unaffected

Caernarfon Threatened

Owain Glyndwr and his forces threaten Caernarfon and Castle

Battle of Tuthill


Good Governance

The Earl of Stafford and the Bishop of Saint Asaph are commissioned to establish measures for the safe custody and good governance of North Wales

Ruthin Raided

Glyndwr's men raid Ruthin and carry off spoils including cattle


Hotspur is appointed the Lieutenant of North Wales. Thomas Percy the Earl of Worcester is appointed Lieutenant of South Wales

Captive Taken

Reginald Grey is captured by Glyndwr's men in an ambush. It is possible that he was betrayed by his own household

Castles Garrisoned

Castles are repaired (including Kidwelly and Monmouth) and garrisons are maintained (including Carreg Cennen)

Battle of Bryn Glas (Pilleth)

Welsh forces led by Glyndwr himself beat the Herefordshire levy led by Edmund Mortimer who is captured (later to marry Glyndwr's daughter). This bloody victory (it is alleged that Welsh women mutilated the genitalia of the English dead) builds the reputation of the Welsh as a force not to be lightly dismissed. The site of the battle, in the southern marches is rings warning bells to the English.

Leominster fortified

Walls and ditches are build around Leominster

Lieutenant of Carmarthenshire, Cardiganshire and Brecon

Richard Lord Grey of Codnor given military command of Carmarthenshire, Cardiganshire and Brecon

A new military order

Two new military commands are created along the English border -- in the North under the Earl of Arundel and in the South under the Earl of Stafford


The Prince of Wales leads a force to relieve Harlech and Caernarfon. The Earl of Arundel leads his retinue into Wales. Henry IV leads a force from Shrewsbury into North Wales, destroys Llanwrst Vill but is overwhelmed by the weather and returns home dishevelled. To quote the Monk of Evesham 'he returned home ingloriously'

Homildon Hill

Percy is victorious!


Edmund Mortimer marries Glyndwrs daughter

Welsh Stronghold

North West Wales is a Welsh stronghold. The castles of Beaumaris, Caernarfon, Harlech and Aberystwyth are isolated English outposts, frequently beseiged and supplied by sea


Pressure on the Shropshire march from Welsh rebels. Insurrection in Flintshire

Hope Burns

The town of Hope in Cheshire burns at the hands of Welsh rebels

Prince Hal

16 year old Prince Hal is made Lieutenant of Wales

Hal attacks

Sycarth and Glyndyfrdwy attacked by Prince Hal


Harlech and Aberystwyth in English hands are both under seige. Harlech is relieved by a force of 1300 men of Chesire sent by Prince Hal

Garrison increased

Radnor garrison tripled to 70 men

The men of Tywi revolt 1

Owain Glyndwr leads his army down the Tywi valley, taking the castles of (amongst others) Dryslwyn, Newcastle Emlyn and Carmarthen


Hotspur revolts in Chester

The men of Tywi revolt 2

Contingent of Glyndwr's army is defeated North of Carmarthen

The Battle of Shrewsbury

Hotspur and Thomas Percy Killed...

Cross border raiders

The Welsh of Flintshire raid towns in Shropshire. They lay seige to Flint, Rhuddlan and Hawarden. Fears arise that raids could be extended into Chesire and Herefordshire

Kidwelly attacked

The Welsh of Cydwdi and Carnwgllion mount an attack on Kidwelly castle. Several Englishmen are killed. The same events occur again in October

Rebels hold Carmarthen

Glyndwrs rebels have taken Carmarthen

The Kings Campaign

Henry IV leads a campaign. They take two weeks travelling from Brecon to Carmarthen, where they stay for five days (and leave 550 men for a month) then on to Hereford

Seige Season 1

Cardiff castle is under seige. Forces from France and Brittany aid Henry Don in the seige of Kidwelly castle

Appointments 1

Edward Duke of York (the Kings cousin) is appointed Lieutenant for South Wales for a year

Appointments 2

Richard Earl of Warwick and John Lord Audley are appointed to control Brecon for a year

The French in the fray

The French attack Caernarfon from both land and sea

Seige season 2

Aberystwyth, Caernarfon, Beaumaris, Cardiff & Kidwelly are all under seige. The French are involved at Kidwelly and Caernarfon

Parliament Proclaims

A meeting of parliament places military command of wales in the hands of the Prince of Wales

Powerful Prince

The Prince of Wales is appointed Lieutenant in North Wales. He commands 500 men-at-arms and 3000 archers.


Constable of Harlech Castle is captured. The Deputy Sheriff of Anglesey is captured and his escort is killed. The men of upland Brecon agree to submit to the King if he defeats the rebels in Glamorgan.

Welsh holdings

Aberystwyth (Llanbadarn) & Harlech are in Welsh hands

Even more chaos...

Raids, burnt villages & mills, cross border raiding...


The Welsh are defeated at Grosmont

Order Order!

A parliament is held at Machynlleth

Bonjour monsieur!

A Welsh diplomatic mission is sent to France.

Let's be friends

A Franco-Welsh treaty is concluded.

Kidwelly roasted

Kidwelly town is captured and burnt

Run Run...!

Welsh forces chase Englishmen to the gates of Monmouth.

Ahah Jim Lad!

A naval force is assembled in France to establish a bridgehead


Notable Welshmen begin to defect to Glyndwrs cause -- John Trefor Bishop of St Asaph and Chamberlain of Chester & Lewis Byford Bishop of Bangor


2000 men are posted to seven key castles.

Oh No!

The Welsh are defeated at Usk. Glyndwr's brother is killed and his son captured. His secretary is captured later in the month.


Anglesey is attacked from the sea by the Lieutenant of Ireland.

English Rebellion

Archbishop Scrope's rebellion in England is crushed. The Earl of Northumberland and Lord Bardolf flee to Scotland (then to Wales in 1406).

Seige Season

Rhuddlan castle besieged by the Welsh


A French force arrives at Milford Haven, they chevauche to within 8 miles of Worcester.


Gwilym ap Gruffudd ap Gwilym and brothers Rhys and Robin along with four other Welshmen surrender at Chester.

Order Order Order

The second Welsh parliament is held at Harlech castle.

Coety Relief

Coety castle is relieved by English forces. The men of pembrokeshire bribe the welsh with 200.

Castle Power

English power is concentrated in the royal castles and large garrisons.

New arrivals

The Earl of Northumberland and Earl Bardolf arrive in Wales

A French affair

Owain Glyndwr ratifies an alliance with the French at Llanbadarn.

Naval action

An English force of 40 men-at-arms and 300 archers is dispatched by the boat 'Nicolas of Dublin' from Wirral under the command of John Mainwaring Sheriff of Chester and his brother Ralph to Beaumaris.

Prince of the Principality

The Prince of Wales is appointed lieutenant in North and South Wales and given 5,000 men - he seems reluctant to puruse this task!

North Wales reinforced

Caernarfon's garrison is quadrupled and a naval force deployed to the Menai straits.

An ecclesiastical exodus

Wales' ecclesiastical allegiance is transferred from the Roman Pope (supported by the English) to the Avignonese Pope (supported by the French). The vision was to establish an independant Welsh church and two universities.


The Scottish heir to the throne is captured and held by the English as a guarantor of Scottish diplomatic caution.

A royal guarantor

Hywel Gwynedd and his accomplices are ambushed and killed in Flintshire.

Victory on St Georges day

1,000 Welshmen are killed in battle with the English.

Au Revoir

The remnant of the French forces leave.

A reversal

Edward Charlton and a force from Shropshire trounce the Earl of Northumberland and Earl Bardolf

Men of Flint

Seven leading men of Flintshire are given safe conduct to Chester to make submissions.


220 men posted to guard Anglesey. 60 soldiers guarding the Menai strait.

Show me the money!

The Prince of Wales is given a new commission - less men / more money.

Enquires being held

Official enquiries are being held in St Asaph, Rhuddlan, Holywell, Caerswys to gather information on who had died in the revolt, their lands etc.


2000 men of Anglesey submitted and tried.


Coelion in Dyffryn Clwyd is being devastated by Glyndwrs men.

Order in court

The Anglesey county court has recommenced meeting.

Anglesey subdued

John Mainwaring is appointed the military commander of Anglesey with a force of 100 men.

Trial and retribution

1000 men of Flint appear before Gilbert Talbot and other justices at Flint and agree to pay a large communal fine for their part in the rebellion.

6 months

The Prince of Wales contracted to serve in Wales for 6 months with 600 men-at-arms and 1800 archers.

Campaign supplies

The Prince of Wales is given 7,000 to pursue his campaign.

Seige of Aberystwyth

A seige of Aberystwyth is prepared by the Welsh, Glyndwr takes control of the castle amidst English bickering and lily-livered behaviour.


Gilbert Talbot is given a force of 100 men-at-arms and 400 archers to tour Caernarfonshire and Merionethshire to collect fines imposed at session.

Menai Guarded

20 men-at-arms and 100 archers posted to Caernarfon to guard Menai straits.

Cardiganshire Guarded

480 men posted at Strata Florida to police North Cardiganshire.


English and French form a truce.

Northumberland falls

The Earl of Northumberland and his allies killed at the battle of Bramham moor.

Envoy to Paris

Two envoys are sent to Paris to appeal for help against the English.

Rebels retreated

The rebels have ensconced themselves in the fastness of the Upper Conwy valley, planning to ambush the Chamberlain of North Wales as he travels to Chester.

Castles fall

Aberystwyth and Harlech castles fall to the English

Gam taken

Dayfdd Gam, a Breconshire land-owner who fought with the English during the height of the rebellion, is captured and ransomed. Owain Glyndwr recieves a large ransom. This is the last that is heard of Glyndwr


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