Gupta (ELO 1685) put up an impressive display and matched his illustrious rival Awate (ELO 2135) to force a draw and a division of the point at the Don Bosco High School, Borivali.
In another tightly contested match, young Muktesh Raghavan (ELO 1580) put up a strong show against Shubham Kumthekar (ELO 1945) to steer the game to a draw while Ankit Bhattacharya (ELO 1447) defeated Vedant Panesar (ELO 1849), who was rated nearly 400 points above him.
Top seed IM Vikramaditya Kulkarni, Chirag Satkar, Ketan Boricha and Rajababu Gajengi, all having won all their matches, had 4 points each.
A further group of eight players were trailing the leaders by half-a-point and the list included Awate, Amardeep Bartakke, Pratik Shenvi, Rajesh Gupta, Ravindra Nargundkar, Ankit Bhattacharya, Yash Kapadi and Aditya Bandekar.
Five more rounds remain to be played over the next three days in this tournament.