1389: The Battle of Kosovo. The Ottomans expand across the Balkans and force Ottokar IV to become a vassal of the Sultan, Murad I.
1402: Death of Ottokar IV. He is succeeded by his son Amilkar.
1403: Amilkar I marries Anna Maria Lascarina, a distant relative of the Despot of Epirus.
1404: Birth of a son, Damilkar to King Amilkar and Queen Anna.
1409: King Sigismund of Hungary visits Klow and initiates King Amilkar into the Order Of The Dragon.
1410: Amilkar is forced to supply troops for the army of Süleyman Çelebi during the so-called Ottoman Interregnum. Following an embassy from Musa Çelebi, these troops desert Süleyman's army and join that of Musa. Following the defeat of Musa's army at the Battle of Camurlu in 1413, the Syldavian troops return home, much depleted in numbers. Their leader, Count Vladimir of Tesznik dies on the journey home and his remains are interred in the Basilica of St Budvar in Klow.
1430: The ageing Amilkar expels Hussite supporters from their stronghold in the Zympathian mountains.
1432: Southern Syldavian nobles send troops to join the revolt of Gjergj Arianiti against the Ottomans.
1436: Ali Bey Evrenosoglu, after defeating the Albanian Revolt sends an army to invade Syldavia. Amilkar is forced to abdicate and his son Damilkar is crowned king.
1439: Damilkar I is assassinated by a cabal of nobles. His younger brother Budvar is placed on the throne as King Budvar IV.
1453: Fall of Constantinople. Syldavian troops are present at the Siege as part of the Ottoman army. It is recorded that they quarrel with the Bordurian contingent in the Ottoman army and are disciplined by the Sultan.
1461: Budvar IV dies and is succeeded by his son as Budvar V.
1462: King Matthias Corvinus of Hungary visits Klow on the occasion of the marriage of Budvar V to Anne de Lusignan. Budvar is made a Knight of the Order of the Dragon.
1464: Budvar creates a Syldavian Order of Chivalry, the Order Of The Black Pelican.
1471: The new Pope, Sixtus IV creates the Archbishop of Klow, Istvan Mishderri a cardinal.
1483: Syldavia and Venice renew their Treaty of Perpetual Friendship. The Venetian Fondaco in Dbrnouk is rebuilt and extended in size. The fortress of Dbrnouk is strengthened.
1494: Syldavian stradiots and crossbowmen form part of the Venetian forces when Charles VIII invades the Italian peninsula. They take part in the Battle of Fornovo in 1495.
1501: Budvar V dies. His son is crowned Ottokar V.
1506: Ottokar V is killed during a joust. His son succeeds him as Ottokar VI. Until he comes of age when he is 18, the country is ruled by Queen Sophia and Count Balonyi of Smyntz.
1515: Ottokar VI marries Maddalena Foscari, the daughter of a noble Venetian family.
1516: Ottokar VI comes of age. His coronation is attended by representatives of the Holy Roman Emperor, Maximilian I, King François I of France and Ottoman Sultan Selim I. Despite the great show of wealth and power, Ottokar is once again compelled to submit to being a vassal of the Sultan.
1518: Queen Maddalena gives birth to twin daughters, Aurelia and Isabella.
1521: Queen Maddalena gives birth to a son, Ottokar Maximilian.
1536: Aurelia of Almaszout marries Ferdinand of Grimmelshausen, a member of the extended Habsburg family.
1537: Isabella of Almaszout marries Sigismond Sirokay, a Transylvanian nobleman.
1541: Ottokar Maximilian marries Theodora Palaiologína, a Transylvanian member of a family descended from the Greek emperors.
1544: Ottokar VI proclaims the doctrine of Syldavian Reformation, which allows the practice of Lutheran Christianity while asserting the primacy of the Roman Church.
1553: Ottokar VI perishes at sea when his state galley is sunk in a storm. He is succeeded by his son as Ottokar VII.
1560: Ottokar VII is commanded to supply galleys to fight for the Ottoman fleet which defeats a Christian alliance at the Battle of Djerba. The commander of the Syldavian contingent mutinies and his squadron of seven galleys become pirates.
1564-66: Conflict erupts between Catholics and Lutherans and a state of civil unrest exists until the arrest and execution of the leaders of the militant Lutheran faction.
1571: Ottokar VII dies from over-eating and a dissolute life. He is succeeded by his son Budvar VI.
1594: Budvar VI declares an Edict of Tolerance to prevent civil war between Lutherans and Catholics. Civil strife immediately breaks out in a number of cities, including Istow and Douma.
1597: The religious wars end following the Siege of Douma and the defeat of the Catholic Black Pelican League.
1601: Budvar VI is assassinated by a fanatical Catholic monk. He is succeeded by his son, Muskar, who becomes Muskar III.
1612: Muskar III is killed when his horse bolts and he is thrown.
1612: Ottokar VIII is crowned in Klow. At his coronation he marries Anne-Louise von Strelitz, a Ruritanian princess.
1618: The Thirty Years' War breaks out. Many Syldavian volunteers enlist on the Imperialist side.
1639: Ottokar VIII dies. He is succeeded by his son, Budvar.
1642: Budvar VII expels Ottoman merchants and political agents from the kingdom. Usman Pasha, Hospodar of Borduria sends an army to punish the Syldavians. The eastern city of Pelmitz is besieged and the inhabitants slaughtered or led off in chains.
1664: Budvar VII dies. His son is crowned Muskar IV.
1667: Muskar seeks an alliance with the Austrians.
1681: Muskar expels all Ottomans from the kingdom. An Ottoman punitive expedition is defeated by the rag-tag Syldavian army, bolstered by Venetian and Austrian mercenaries.
1683: Muskar IV is killed leading his troops in the Polish army at the Siege of Vienna. He is succeeded by his son as Muskar V. Muskar reigns for 48 years, outliving both his sons.
1684: Muskar marries Charlotte Maria of Strudel, an Austrian noblewoman.
1687: Syldavia throws off the last vestiges of Ottoman suzerainty following the Second Battle of Mohács. The king begins the process of modernising his kingdom. He invites the Austrians to send advisers and experts to build up his army.
1699: The Austrian Graf von Seltzer is appointed Captain-General of Syldavia.
1720: Queen Charlotte dies.
1720: Queen Charlotte dies.
1721: Muskar marries for a second time. His new wife is the much younger Elizabeth Augusta of Strackenz.
1731: Muskar V dies and is succeeded by his grandson as Ottokar IX. A regency led by Queen Dowager Elizabeth Augusta and her lover Count Sszsenyhawkz rules until Ottokar comes of age.
1734: Ottokar marries the French princess Octavie de Bourbon.
1735: Ottokar comes of age. His first act is to banish Count Sszsenyhawkz and Queen Elizabeth Augusta.