Battle of Chakan The Battle of Chakan was fought between the Maratha Empire and the Mughal Empire in the year 1660 . Shaista Khan was ordered by Aurangzeb to attack Shivaji per the Mughal - Adilshahi accord . Shaista Khan , with his better equipped and provisioned army of 150 , 000 that was many times the size of the Maratha forces , seized Pune and the nearby fort of Chakan . At the time , Firangoji Narsala was the " killedar " ( commander ) of fort Chakan , which was defended by 300 – 350 Maratha soldiers . They were able to withstand the Mughal attack on the fort for one and a half month . The Mughal force was numbering over 21 , 000 . Then , a " burj " ( outer wall ) was blown up with explosives . This created an opening to the fort allowing hordes of Mughals to breach the exterior portion of the fort . Firangoji , himself led the Maratha counterattack against a larger Mughal army . Eventually , the fort was lost with the capture of Firangoji , who then was brought before Shaista Khan , who , appreciating his bravery , offered him a " jahagir " ( military commission ) on the condition that he join the Mughal forces , which Firangoji declined . Admiring his loyalty , Shaista Khan pardoned Firangoji and set him free . Firangoji returned home and Shivaji awarded him a fort named Bhupalgad . Shaista Khan pressed his advantage of larger , better provisioned and heavily armed Mughal army and made inroads into some of the Maratha territory . Although he held Pune for almost a year , he had little further success . He had set up his residence at Lal Mahal , Shivaji ' s palace , in the city of Pune . Shaista Khan kept a tight security in Pune . However , Shivaji planned an attack on Shaista Khan amidst tight security . In April 1663 , a wedding party had obtained special permission for a procession ; Shivaji planned an attack using the wedding party as cover . The Marathas disguised themselves as the bridegroom ' s procession and entered Pune . Shivaji , having spent much of his youth in Pune , knew his way around the city and his own palace of Lal Mahal . Chimanaji Deshpande - one of the childhood friends of Shivaji aided him in this attack offering his services as a personal bodyguard . According to Babasaheb Purandare , since Mughal army also consisted of Maratha soldiers , it was difficult for someone to distinguish between Shivaji ' s Maratha soldiers and the Maratha soldiers of the Mughal army . Thus , taking advantage of this situation , Shivaji , along with a few of his trusted men , infiltrated the Mughal camp . After overpowering and slaying of the palace guards , the Marathas broke into the mansion by breaching an outer wall . Chimnaji and Netaji Palkar entered first along with Babaji Deshpande , another of Shivaji ' s long time loyal associates , they approached Shaista Khan ' s quarters . Shivaji then personally confronted Shaista Khan in a face to face attack . Meanwhile , perceiving danger , one of Shaista ' s wives turned off the lights . Shivaji pursued Shaista Khan and severed three of his fingers with his sword ( in the darkness ) as he fled through an open window . Shaista Khan narrowly escaped death and lost his son and many of his guards and soldiers in the raid . Within twenty - four hours of this attack , Shaista Khan left Pune and headed north towards Agra . An angered Aurangzeb transferred him to distant Bengal as a punishment for bringing embarrassment to the Mughals with his ignoble defeat in Pune .