Battle of Călugăreni The Battle of Călugăreni was one of the most important battles in the history of early modern Romania . It took place on 23 August ( 13 August on old style calendar ) 1595 between the Wallachia n army led by Michael the Brave and the Ottoman army led by Sinan Pasha . It was part of the Long War , fought between Christian and Ottoman forces at the end of the 16th - beginning of the 17th centuries . The whole Ottoman forces were estimated at about 100 , 000 men , but not all of their troops were on the battlefield at Calugareni . It seems that about 30 , 000 - 40 , 000 Ottoman soldiers were involved in the battle . Michael the Brave had in total about 16 , 000 men and 12 large field cannon , with Transylvanian ( Székely ) detachments . Being heavily outnumbered , Michael the Brave strategically positioned his forces near a swampy field ( near Neajlov River ) that would negate the Ottoman ' s military superiority . South of the village of Călugăreni , where the Câlniştea river flows into Neajlov river , the terrain is a muddy marsh , surrounded by forests . A narrow bridge over the Neajlov river was a mandatory pass point . The battle had three different phases . First phase of the battle . The day of 23 August 1595 started with probing cavalry attacks . The Wallachian cavalry surprised the Ottoman cavalry in front of the village and pushed it over the Neajlov river . Michael the Brave positioned himself with 10 , 000 troops and 10 cannons north of the Neajlov river and south of the village . The Székely mercenary Captain Albert Király was in charge of the reserve of 6 , 000 Székely troops . The reserve was positioned rather far , north - west of the village , to stop any possible attack from the direction of the village of Singureni . After the cavalry skirmish , Sinan Pasha sent forward a force 12 , 000 strong . Michael the Brave waited for the Ottoman forces to cross the river and , after a heavy artillery bombardment , attacked fiercely pushing the Turks back over the river . The first phase of the battle ended favorably for Wallachians . Second phase of the battle . The second phase started at noon , when Sinan Pasha launched a decisive attack with all the forces he had at that moment . Janissaries made a frontal attack over the bridge while other forces made a double flanking maneuver ( Mehmet Satîrgi Pasha in the east and Hasan Pasha ( beylerbey of Rumelia ) in the west ) . Janissaries attacked not only on the bridge , but also used logs and planks to help them cross the marsh . Initially their attack was stopped , but Ottoman cavalry managed to cross the river via a ford in the east and threatened the Wallachian left wing . Michael retreated , abandoning all his cannons . He rallied his troops north of the village where he stopped the Ottoman advance . The second phase of the battle ended favorably for Ottomans . Third phase of the battle . The third and last phase of the battle took place in the afternoon of the day and started with a strong frontal Wallachian attack , led by Michael the Brave . Captain Cocea had just returned from a scouting mission with 400 cavalry and his fresh forces were used in this attack in a flanking maneuver . Mehmet Satîrgi Pasha ' s troops were pushed into the Janissaries and the Ottoman forces were crowded in a narrow space north of the Neajlov River . The Wallachian counterattack reached the bridge and the cannons were retaken and used to inflict many casualties to the Ottomans . Sinan Pasha tried to restore the situation by advancing with his personal guards , but the Ottoman forces went in disarray when captain Cocea ' s cavalry attacked them in the rear . Wallachians attacked simultaneously the Ottoman camp , which was near the Hulubeşti village . In the disorganized retreat , here legend has it that Michael the Brave true to his name took a battle axe and ( as Robert the Bruce had done to sir Henry de Bouhen at the battle of Bannockburn ) threw Sinan Pasha from his horse and into the marsh , but he was saved by one of his slaves . The Wallachians were unable to pursue the fleeing Ottomans because Hasan Pasha appeared on their right flank . Michael the Brave turned with all his men against Hasan Pasha and routed his forces . Aftermath of the battle . The casualties are estimated at least 1 , 000 men for Wallachians , while the Ottoman casualties are thought to be in the range of 10 , 000 to 15 , 000 . Michael the Brave knew that he still was greatly outnumbered , and during the night he retreated northward . He abandoned both Bucharest and Târgovişte , stopping at the winter camp in Stoieneşti , near the Rucăr - Bran Pass . Sinan Pasha captured the Capital , Bucharest and left there Mehmed Pasha with 10 , 000 troops , then captured Târgovişte where he left another 1 , 500 troops and 30 cannons . The bulk of the Ottoman army advanced to Stoieneşti , where it took positions in front of the Wallachian army , but didn ’ t attack . On 6 September , the Transylvanian prince Sigismund Báthory arrived with around 7 , 500 cavalry to support Michael the Brave . Early October another 1 , 500 troops from the Habsburg empire and 300 cavalry from Toscana arrived . These combined forces attacked the Ottomans and eventually defeated them at Târgovişte ( 18 October ) , Bucharest ( 22 October ) , and Giurgiu ( 26 October ) . Literature . In Romanian : In Turkish :