| 1136 | | King Stephen captures Bampton |
| | | Bampton Castle in Devon captured by King Stephen. |
| 1138 | | Ludlow castle siege |
| | | Ludlow Castle was captured on behalf of Matilda in 1138 and King Stephen besieged the castle in an attempt to regain it. During the siege the King bravely saved Prince Henry of Scotland from being injured by a grappling hook thrown from the castle. |
| | Dudley castle attacked by Stephen |
| | | The Castle and lands around Dudley were attacked by King Stephen during the early part of his war against Matilda. |
| | Shrewsbury Castle captured by Stephen |
| | | Stephen captured the castle at Shrewsbury. Henry (II) would capture back the castle before the end of Stephen's reign. |
| | Arundel Castle siege |
| | | Matilda was given refuge by William de Albini at Arundel Castle. Stephen built siege works around the castle in response. |
| | Start of Civil War |
| | | Robert, the Earl of Gloucester and half brother to Matilda (daughter of Henry I) rebels against King Stephen, supporting Matilda's claim to the throne of England. |
| May | Robert sides with Matilda |
| | | Robert, the Earl of Gloucester announces that he will assist Matilda, his step-sister in her claim for the English throne. |
| 1139 | | Wallingford Castle siege |
| | | After Brian fitz Count the owner of the castle at Wallingford sided with Matilda, king Stephen built two siege castles to force him out. |
| | Matilda arrives in England |
| | | Matilda arrives in England to further her attempts to take the throne from king Stephen. |
| 1140 | | Woodstock held by Matilda |
| | | The Palace of Woodstock was held by Matilda's supporters during the conflict with Stephen. Henry (II) spent much of his time there. |
| 1141 | | Winchester Castle burns down |
| | | The castle was destroyed during the civil war. |
| Feb 2 | Battle of Lincoln |
| | | Matilda's forces defeated and captured King Stephen at the battle of Lincoln. Stephen was held captive until September when Matilda's forces were defeated at Winchester. |
| Apr | Matilda is elected Queen |
| | | After Stephen had been captured at Lincoln, Matilda was elected as Queen of England at Winchester. Her new position as ruler of England was not to last for long |
| Jun | Matilda enters London |
| | | Matilda and her supporters entered London for her coronation. Her supporters included David I, king of the Scots. Geoffrey de Mandeville who controlled the Tower of London, abandoned his king as he saw Matilda had the upper hand. He joined her side and offered her the Tower of London. He did this to ensure he kept the Earldom of Essex which made him one of the most powerful barons of the time. |
| Sep 14 | Rout of Winchester |
| | | Matilda's forces were besieging a royalist held castle at Wolvesey near Winchester and were attacked and defeated by a royalist relief army. King Stephen who was being held captive at the time was exchanged for Robert, earl of Gloucester one of Matilda's supporters who was captured in the defeat. |
| 1142 | | Mandeville and Matilda |
| | | Secret negotiations between Matilda and Mandeville take place. |
| | Henry (II) spends a year in England |
| | | Henry spent a year in England at Bristol being taught by Master Matthew. He came across the channel with Earl Robert of Gloucester. |
| 1143 | Sep | Mandeville is arrested |
| | | King Stephen arrested Geoffrey de Mandeville at a meeting of the Royal Court. Mandeville had tried Stephen's patience with his disloyalty and the king did not want the Tower of London (which Mandeville controlled) fall into the hands of Matilda. Mandevilles castles and title of Earl of Essex were taken from him, and he became an outlaw. |
| 1144 | | Construction of Faringdon Castle |
| | | Built by Robert, Earl of Gloucester. The castle soon came under siege by King Stephen who after four days took the castle and destroyed it. |
| 1145 | | Stephen takes Farringdon Castle |
| | | King Stephen captures the castle at Farringdon from Matilda. |
| 1147 | Oct 31 | Robert, Earl of Gloucester dies |
| | | The death of Robert was a blow to Matilda's attempts to fight for the English throne. Matilda was to leave England shortly afterwards. |
| | Henry arrives in England |
| | | Henry landed in England with a small army intent on attacking Stephen. Unfortunately, Henry's army of mercenaries was small and they were not being paid enough. Stephen gave Henry money to pay the mercenaries and for Henry to return to Normandy. Henry left England. |
| | Pevensey Castle siege |
| | | King Stephen leys siege to Pevensey castle and has to wait for the castle's reserves to run out before the castle falls. |
| 1148 | Feb | Matilda leaves England |
| | | Without the support of the Earl of Gloucester, who died the previous year, Matilda left England for Normandy. |
| 1149 | May 22 | Henry (II) knighted by David |
| | | Henry the future king of England (Henry II) was knighted at Carlisle by David, King of the Scots. |
| 1152 | | Newbury Castle Siege |
| | | Besieged and captured by King Stephen in 1152 (or 1153). |
| Apr 6 | Theobald refuses to crown Eustace |
| | | King Stephen had several lords swear to have Eustace, his son, as the next king of England. Theobald the Archbishop of Canterbury, who had to accept as well, refused to crown Eustace favouring Henry II's claim to the throne instead. |
| 1153 | | Reading Castle destroyed |
| | | Reading Castle destroyed by Henry II. |
| Jan | Henry invades England |
| | | Henry and a fleet of 30 to 40 ships landed on the south coast of England. Henry chose to attack Malmesbury, one of Stephen's out posts. The Winter weather took its toll on Stephen's troops and a truce was agreed. In the Midlands, the Earl of Leicester took Henry's side and this gave Henry control of large number of castles in the area. |
| Aug 17 | Stephen's son Eustace dies |
| | | Eustace wanted to continue the fight against Henry and had started attacking areas around Cambridge and East Anglia. He ransacked the Abbey at Bury St. Edmunds but died very shortly afterwards from a sudden illness. |
| Nov 6 | Treaty of Wallingford |
| | | Henry had besieged a fort that Stephen had built at Crowmarsh on the banks of the Thames opposite Wallingford Castle. An agreement of succession of Henry II after Stephen was concluded and witnessed by the English Knights Templars. King Stephen accepted Henry of Normandy, Anjou and Aquitaine as heir to the throne and in turn Henry recognised Stephen as king. Stephen made his barons do homage to Henry (Jan.1154). |
| 1154 | Spring | Henry returns to Normandy |
| | | A triumphant Henry returned to Rouen in Normandy to a warm reception from his family including Eleanor and his eight month old son William. |
| Oct 25 | Stephen dies |
| | | Stephen had agreed that Henry should become King on his death. Henry was in Normandy at the time. |
| Dec | Henry II succeeds Stephen |
| | | Under Henry II, the Grand Master of Knights Templars superintended the Masons. 1155 - Built their Temple in Fleet Street. |
| Dec 8 | Henry lands in England |
| | | Although the English Channel was stormy, Henry needed to get to England as it had been without a King since the end of October. His ship landed somewhere near Southampton and he went straight to Winchester where he received the Royal treasures and the homage of the English barons. |
| Dec 19 | Henry crowned at Westminster Abbey |
| | | Henry of Normandy crowned Henry II of England, and Eleanor of Aquitaine crowned Queen, at Westminster.
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