He was posthumously conferred the Maha Vir Chakra, India's second highest war-time military honour, for his actions during the 1999 Kargil War (Operation Vijay).

[6][7] This, like so many later operations in Kargil, was a dangerous mission that required an uphill accent toward the entrenched enemy posts with the benefit of vertical position and good vantage point.

Major Vivek Gupta was in command of the leading Charlie Company, when 2nd Rajputana Rifles launched a battalion attack on Tololing Top, in Drass sector on 13 June 1999.

In spite of heavy artillery and automatic fire, the company under the leadership of Major Vivek Gupta was able to close in with the enemy.

Major Vivek Gupta displayed conspicuous gallantry and inspiring leadership in the face of the enemy, which, ultimately led to the capture of Tololing Top.