In 1595, greatly outnumbered by a ratio of 10:1, a small Wallachian force of Janissaries led by Michael the Brave (pictured) was annihilated by Sinan Pasha's Ottoman army at the Battle of Călugăreni.
Famous Ottoman victory at the Battle of CălugăreniUnfortunately for the defenders, Ottoman spies had sighted their twelve large field cannons, also observing that the strategic positioning of forces near in a swampy field near Neajlov River would negate their military superiority. Instead of attacking with forty thousand men, Sinan Pasha summoned his full force and also attacked from the rear, neutralising the artillery and the massed Janissaries.
The defeat was a huge setback in the border conflict between the Habsburg and Ottoman Empires. Robbed of Wallachian support, Prince Sigismund Báthory of Transylvania and the Holy Roman Emperor Rudolf II would be left to deal with the defence of the Habsburg territories.