The first siege of Anandpur was a thirty-five-day-long siege at Anandpur led by the Rajas of the Sivalik Hills and the Gujar and Ranghar tribesmen against the armies of the Sikh under Guru Gobind Singh.
Prelude
The hill Rajas were concerned about Guru Gobind Singh's rising power and influence in their region. The Mughal generals had failed to subdue the Guru in the Battle of Anandpur (1700). The Rajas appealed to Mughal emperor Aurangzeb to aid them. Raja Bhup Chand of Hundar opposed seeking the aid of the emperor. He insisted the Rajas should be able to win themselves. The Rajas of hill states, Jammu, Nurpur, Mandi, Bhutan, Kullu, Kionthal, Guler, Chamba, Srinagar, Dadhwal, Hindur, Jaswan, Bilaspur, Kangra, Bijarwal, Darauli, and Sirmur, met in council under Ajmer Chand. Ajmer Chand convinced the council to follow him. Ajmer Chand recruited the Gujjars and Ranghars, both of whom had previous hostilities with the Gurus. They were led by Jagatullah.
Ammunition was distributed amongst the Rajas, and they began to march at night.
They sent a letter to the Guru, asking him to pay the arrears of rent for Anandpur (which lay in Ajmer Chand's territory) or leave the city. The Guru insisted that the land was bought by his father and was his property.
Duni Chand led five hundred men from Majha region to assist the Guru. Reinforcements from other areas also arrived to help the Guru.
Siege
Day one
The Rajas and their allies besieged Anandpur. The Sikhs had taken positions in the forts at Holgarh (Agamgarh), Fatehgarh, Taragarh, Keshgarh, and Lohgarh. The Guru ordered them to stay on the defensive. Sher Singh and Nahar Singh, with 500 soldiers each, guarded Lohgarh while Bhai Udai Singh with the men of Duni Chand took Fatehgarh. Ajit Singh with 100 soldiers guarded Taragarh.
Raja Ajmer Chand with others launched an attack on Taragarh first where Ajit Singh was stationed. A fierce battle ensued. Many Sikhs were killed, and Raja Ghumand Chand of Kangra was wounded. The Sikh managed to hold off the Mughals.
Later the first day, the rajas fired cannons on the Guru's forts. Raja Kesari Chand of Jaswan with his troops, the Gujars and the Ranghars attacked Lohgarh and the outposts of Udai Singh. The attacking force was 100,000. Arrows and bullets rained down, and the attacking army had lost half of its strength. The Gujars and Ranghars were on the verge of retreat, but Jagatullah managed to rally his men and they launched a fierce counterattack. Seeing this, Ajit Singh with his troops numbering 100, joined Udai Singh. Kesari Chand and Jagatullah's troops were forced to retreat.
Following defeats on the first day, the Rajas held a council. The Rajas had planned to launch a three-sided attack. Kesari Chand would attack from the right flank and Jagatullah would attack from the left flank. Ajmer Chand would attack from the front.
The Rajas and allies began to execute the plan. Kesari Chand began his attack first. Kesari Chand had under his command an army of 100,000. The army face the Sikhs who were led by Ajit Singh and Udai Singh. Sahib Singh headed to Agamgarh, also known as Holgarh, where Jagutullah with a large army was attacking. Soon after, Jagatullah would be shot in the head by Sahib Singh and died. A Nishan Sahib was planted near the body. Ghumand Chand led the alliance troops to attack the location of Jagatullah's body. Bhai Maan Singh defended. A great massacre ensued as Sikhs defended their position. For 9 hours, Ghumand Chand and his allied forces fought before falling back for rest, and the Sikh captured the body of Jagatullah. After this victory Guru Gobind Singh gave a farla to Bhai Dharam Singh, Bhai Alam Singh, and Bhai Maan Singh. He also gave rewards to other Sikh who fought.
The Rajas again held a council at night, in which Ajmer Chand proposed reconciliation with the Guru. Many Rajas agreed, but Raja Kesari Chand of Jaswal and Raja Bhup Chand opposed the proposal, and suggested a more determined fight the next day, to oust the Guru from Anandpur.
Day two
In the early morning of day two, the Sikhs fired cannons and musket at the camps of the Rajas which forced them to move back.
Next day, Ajmer Chand launched a fierce attack on Fatehgarh with a do-or-die mentality. Fatehghar was still in construction with one of its walls only being half made. Bhagwan SIngh was one of the commanders of the fort. A five-hour battle ensued where many soldiers on both sides died. Bhagwan Singh died in this battle.