[4] Sengupta achieved his first norm for the title Grandmaster (GM) in the World Junior Chess Championship in Kochi, India in December 2004[2] and won the Indian juniors title in 2005.

[2] In 2010, he tied for the top position with Tigran Gharamian and Vadim Malakhatko at the 24th Open "Pierre and Vacances"[6] in Cannes,[7] thereby completing the requirements for the Grandmaster title.

[2] He tied for first with Arghyadip Das in the 2010/11 Hastings Masters tournament and won the event on tiebreak.

[8] In 2011 he tied for 2nd–7th with Maxim Turov, Viacheslav Zakhartsov, Krisztian Szabo, Lev Gutman, Dávid Bérczes and Samuel Shankland in the ZMDI Open in Dresden.

Sengupta won the 2014 Commonwealth Chess Championship, held in Glasgow, edging out Aravindh Chithambaram on tiebreak score.