| 1187 | Jul 3 | Army of Jerusalem defeated |
| | | The army of Jerusalem was beaten by Turkish forces. Guy of Lusignan was King of Jerusalem at this time. All Knights Templars and Hospitallers who survived the battle were executed afterwards. |
| Sep | Saladin captures Acre |
| | | After a short siege Saladin captured the port of Acre from the Christians. |
| Oct 2 | Jerusalem falls to the Muslims |
| | | The al-Asqu mosque was returned to Islam. The Muslims allowed four Christian Priests to hold services in the Church of the Holy Sepulche. This was opposed to the first Crusaders who since they first captured the city in 1099 had treated Jerusalem as theirs alone. The Muslim leader was Al-Malik al-Nasir Salad ed-Din Yusuf (Saladin). |
| Nov | Richard takes the Cross. The Crusade |
| | | Richard took the Cross. Before going on a Crusade a vow was taken and the person was given a piece of cloth in the shape of a cross to be sown onto the surcoat. To go on a Crusade meant a person was granted a plenary indulgence which freed them from the terrors of purgatory and hell if they killed the enemy and gave them the promise of eternal life in heaven. |
| 1190 | Jun 24 | Richard at Tours |
| | | Richard was given the pilgrim's scrip (a bag for the journey) and staff by the archbishop of Tours in preparation for his Crusade. These items were traditionally carried by pilgrims. |
| Jul 3 | Meeting at Vézelay |
| | | Richard I and Philippe II, Augustus, met at Vézelay and agreed to divide the spoils of the Crusade equally between themselves. They planned to take different routes, Richard via Marseilles and Philippe via Genoa. Richard has around 100 ships at his disposal. Several were from the Cinque Ports, others from Shoreham and Southampton and others donated by private persons. Other ships were hired from ports in Normandy. Richard could have had a force of around 8000 men half of which could have had horses. |
| Jul 4 | Richard's Crusade starts |
| | | Richard leaves to begin his crusade. |
| Sep | Messina |
| | | Richard was in no hurry to reach the Holy Land as he had an issue to resolve in Italy first. William II, the King of Sicily, had recently died. He was married to Richard's sister, Joan, who was bequeathed a large dower, a payment meant to support her if she outlived her husband. William had also bequeathed a large sum of money to Henry II, the king of England. Through force, Tancred of Lecce claimed the throne of Sicily and imprisoned Joan refusing to pay the money to her or the King of England. When Richard arrived in Messina he demanded that his sister should be released and all the money owing should be paid. |
| Oct | Richard captured Messina |
| | | The people of Messina, supporting Tancred, shut the gates on Richard and attacked his soldiers. In the harbour French ships turned against Richard as the friendship between Richard and Philippe had broken down because Philippe believed Richard was about to refuse to go through with his marriage to Alais, Philippe's half-sister. This was true as Richard had arranged a marriage to Berengaria of Navarre who was travelling to meet him. Richard's men stormed Messina and captured the town. Richard was lenient on the people of Messina and decided to build a fort overlooking the town. Tancred agreed to pay the money owed, freed Joan from prison and paid Richard a large amount of gold. Friendly relations were restored between Richard and Philippe when Richard agreed to split the gold with the French king. |
| Christmas | Crusaders in Sicily |
| | | Richard and Philippe stayed in Sicily over the winter months waiting for the weather to improve before continuing their journeys to the Holy Land. |
| 1191 | Mar 30 | Philippe leaves Sicily |
| | | The King of France set sail for the Holy Land a few days before Richard. |
| Apr 10 | Richard's fleet leave Sicily |
| | | The fleet left Sicily to sail to Rhodes. On route, three ships were separated from the group and landed on Cyprus at the port of Limassol. The governor of Cyprus at the time was Isacc Dacus Comnenus, who had come to power from trickery. He had sided with Saladin, and treated Richard's ships as the enemy. |
| Apr 20 | Philippe Augustus arrives in Acre |
| | | Philippe Augustus landed in Acre in an attempt to remove Guy of Lusignan as the King of Jerusalem, and replace him with Conrad of Montferrat. |
| May 6 | Richard sails to Cyprus. |
| | | Richard located the three lost ships at Limissol, and promptly attacked Comnenus' troops in the town and drove them out. Comnenus was again attacked outside the town, but escaped, leaving behind his standard, embroidered with gold cloth. This was later presented to the abbey of Bury St. Edmunds. |
| May 11 | Meeting in Limassol |
| | | Richard met Guy of Lusignan (King of Jerusalem), Geoffrey (Richard's brother), Bohemund (Prince of Antioch), Raymond (Count of Tripoli), Humphrey of Toron and other knights to discuss the attempt by Philippe II of France to replace Guy of Lusignan with Conrad of Monferrat as the King of Jerusalem. |
| May 12 | Richard marries Berengaria |
| | | Richard took time to marry Berengaria at Limassol. |
| Jun 1 | Richard controls Cyprus |
| | | By the 1st of June, Richard had control of the whole of Cyprus and imposed a 50% tax in return for letting the Cypriots return to a more traditional way of life. Richard of Camville and Robert of Turnham were left in charge of Cyprus. |
| Jun 6 | Richard arrives at Tyre and attacks Acre |
| | | Richard landed at Tyre and quickly moved towards Acre, where he needed to help an army that was besieging the town which was being held by a garrison of Saladin's troops. By July 12th, the town fell to Richard. Richard held Saladin's men hostage in exchange for 200,000 dinars and 1500 of Richard's own troops who were being held by Saladin. When no ransom was paid, Richard publicly executed 2700 of the garrison. It was at this point that Richard angered Leopold of Austria, who was to imprison Richard as he tried to return to Normandy. Leopold's banner was ripped down from alongside Richard's and the French. The banners indicated that the spoils of war should be shared, but Richard was not prepared the share with Leopold, who had not contributed that much to the fall of Acre. |
| Jul | Richard takes Acre |
| | | Under Richard's command, the city of Acre is taken back by the Crusaders. |
| 1192 | Apr 28 | Conrad is assassinated |
| | | Conrad of Montferrat was killed by two Assassins disguised as monks as he walked home. The Assassins, one of whom had been captured alive and questioned, had been sent by their leader Sinan. The suspected reasons for the murder are varied, some theories suggest Conrad had intercepted a shipment of wealthy goods bound for the Assassin Order while others suggest Saladin had ordered the murder of both Conrad and Richard I. Some also suggest it was Richard himself who had ordered the murder. |
| Oct 9 | Richard I leaves the Holy Land |
| | | After the agreement of a peace treaty Richard left the Middle East and began the voyage back to England. |
| Dec | Richard shipwrecked on the way home |
| | | Richard was shipwrecked while returning home from the middle east. |
| 1193 | Feb | Richard captured by the Emperor of Germany |
| | | Richard was captured by the Emperor of Germany, Henry IV after being shipwrecked on the way home after his Crusade. The Emperor demanded a large ransom to set Richard free. |
| 1194 | Mar | Richard returns to England |
| | | Richard I returned to England after his Crusade and imprisonment in Germany. John had all his castles in England confiscated and the only title left to him was that of Lord of Ireland. |