Alauddin Khiliji was the first Delhi Sultan to cross the Vindhya region.
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Of Alauddin's first year as the Sultan, chronicler Ziauddin Barani wrote that it was the happiest year that the people of Delhi had ever seen. At .
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In 1296, Alauddin Khalji (then known as Ali Gurshasp) raided Devagiri, the capital of the Yadava kingdom in the Deccan region of India. At the time, Alauddin was the governor of Kara in Delhi Sultanate, which was ruled by Jalaluddin Khalji. Alauddin kept his march to Devagiri a secret from Jalaluddin, because he intended to use the wealth obtained from this raid for dethroning the Sultan.
When Alauddin reached Devagiri, the Yadava king Ramachandra retreated to the hill fort, and Alauddin's army thoroughly ransacked the lower city. The defenders were under-prepared for a siege, as the Yadava army was away on an expedition under Ramachandra's son Simhana and the fort of Devagiri had insufficient provisions. Therefore, Ramachandra agreed to a peace treaty, offering Alauddin a large sum of money. However, Simhana soon arrived in the capital and engaged Alauddin in a battle. Alauddin emerged victorious, and forced the Yadavas to agree to a peace treaty. This time, the Yadavas were forced to pay a much larger war indemnity, and had to offer the revenues of the Achalpur province to Alauddin as tribute.
Alauddin returned to Kara after spending some days in Devagiri. He subsequently dethroned Jalaluddin, and sent a second expedition to Devagiri in 1308, which forced Ramachandra to become his vassal.