1140 Rhwng Gwy a Hafren
Madog ab Idnerth of Rhwng Gwy a Hafren (Between the Wye and the Severn) died in 1140, and his lands were then ruled by his sons. The Norman Marcher lords made numerous incursions into the area: in 1142, Hywel and Cadwgan ap Madog were both killed by Helias de Say, lord of Clun; and in 1146, Maredudd ap Madog was killed by Hugh de Mortimer. The two surviving sons, Cadwallon and Einion Clud, ended up ruling Maelienydd and Elfael, respectively.
1146 Llansteffan Castle
Llansteffan Castle in Deheubarth was taken by Cadell, Maredudd and Rhys, the sons of Gruffudd ap Rhys ap Tewdwr.
1149 Tomen-y-Rhodwydd
Owain Gwynedd built Tomen-y-Rhodwydd near Llandegla and annexed Iâl and Tegeingl.
1154 Henry II crowned king of England.
1157 Battle of Ewlo
Henry II of England led an army into north-east Cymru to challenge Owain Gwynedd. Henry’s army also included Madog ap Maredudd of Powys, Owain’s brother-in-law. Despite Owain’s forces winning the battle, he was eventually forced to agree terms with Henry II. Tomen y Rhodwydd was then destroyed.
1158 Ifor Bach of Senghennydd
Ifor ap Meurig - or Ifor Bach - of Senghennydd killed Morgan ab Owain of Gwynllwg and Caerlleon in battle, and also broke into Castell Caerdydd and captured William FitzRobert, earl of Gloucester, and his family. He then forced the earl to restore conquered lands and donate further lands to him in recompense.
1160 Death of Madog ap Maredudd
Madog ap Maredudd died in 1160 and Powys was split into two parts: Powys Fadog in the north and Powys Wenwynwyn in the south. Madog’s death also allowed Owain Gwynedd to regain lands in the north-east.
1163 Treaty of Woodstock
Owain Gwynedd formed an alliance with his nephew, Rhys ap Gruffudd of Deheubarth, in response to restrictions imposed by Henry II in the treaty of Woodstock. Rhys had already regained Deheubarth and built the stone castles of Aberteifi and Carreg Cennen.
1165 Battle of Crogen
Henry II eventually led an invasion into Cymru, and Owain Gwynedd responded by assembling many of the rulers of Cymru at Corwen. The Cymry were victorious at the battle of Crogen and this was the last time Henry invaded Cymru. Owain went on to take Basingwerk, Rhuddlan and Prestatyn, and extended Gwynedd’s rule from Ynys Môn to the Dee Estuary. He was the first person to call himself Tywysog Cymru.
1170 Death of Owain Gwynedd
Owain Gwynedd’s nominated heir was his son, Hywel, but this was contested by his other sons after Owain’s death in 1170, however. Rhys ap Gruffudd of Deheubarth (Yr Arglwydd Rhys) became the chief ruler in Cymru following Owain’s death.
1170 Battle of Pentraeth
Hywel ap Owain Gwynedd was defeated and killed by his half-brother, Dafydd ab Owain Gwynedd, at Rhos-y-gâd near Pentraeth towards the end of 1170. Dafydd eventually seized power by disposing of his other half-brothers and finally his blood-brother, Rhodri.
1170 Battle of Pant Cadifor
According to local lore, Ifor ap Meurig (Ifor Bach) of Senghenydd was also killed in battle at Pant Cadifor near Merthyr Tudful. Ifor was the brother-in-law of Rhys ap Gruffudd of Deheubarth.
1172 Rhys ap Gruffudd
Rhys ap Gruffudd (Yr Arglwydd Rhys) of Deheubarth was appointed justice of De Cymru by Henry II, making him the chief ruler in Cymru.
1175 The Abergavenny Massacre
William de Braose invited Seisyll ap Dyfnwal of Castell Arnallt, and other leaders from Gwent, to Castell Y Fenni (Abergavenny) to celebrate Christmas. After the Cymry had relinquished their weapons at the door, they were massacred in the great hall of the castle by De Braose’s men. A few years later, Hywel ap Iorwerth, lord of Caerleon, ordered the burning of Castell Y Fenni in retribution for the murder of Seisyll.
1176 Eisteddfod Aberteifi
Rhys ap Gruffudd founded Talley Abbey and Llanllyr nunnery, and also held an eisteddfod at Castell Aberteifi.
1179 Cadwallon ap Madog
Cadwallon ap Madog had become sole ruler of Rhwng Gwy a Hafren on the death of his brother, Einion Clud, in 1176. Cadwallon was known for building castles on his lands, and also the abbey, Abaty Cwm-hir. He was killed in 1179 by the men of Roger Mortimer of Wigmore, however, despite being under a royal safe conduct from Henry II of England. Mortimer was then imprisoned for two years.
1188 Gerallt Cymro
In 1188, Gerallt Cymro (Gerald of Wales) accompanied the archbishop of Canterbury on a journey through Cymru to recruit volunteers for the Third Crusade. Owain Cyfeiliog of Powys Wenwynwyn refused to support the visit and was consequently excommunicated. An account of this tour, ‘Itinerarium Cambriae’, was published by Gerallt in 1191.
1194 Battle of Aberconwy
Llywelyn ap Iorwerth then came to prominence in Gwynedd. He was a grandson of Owain Gwynedd and, at the battle of Aberconwy, he defeated his uncles, Dafydd and Rhodri ab Owain; Llywelyn was supported by his cousins, Gruffudd and Maredudd ap Cynan.
1194 Battle of Porthaethwy
Rhodri ab Owain died later that year after his defeat to his nephew, Llywelyn, at the battle of Porthaethwy.
1196 Battle of Maesyfed
Rhys ap Gruffudd of Deheubarth attacked and burned Castell Maesyfed (New Radnor) and then drove to flight a Norman force, led by Roger de Mortimer and Hugh de Sai.
1197 Death of Rhys ap Gruffudd
Rhys ap Gruffudd died unexpectedly in 1197 and was buried in Tyddewi (St Davids). His death led to conflict between his sons for the control of Deheubarth, particularly between his legitimate son and heir, Gruffudd, and his illegitimate son, Maelgwn.