[8][9][10][11] He joined then Calcutta Football League side Mohun Bagan in 1921 and was part of the "golden era" of the club during British rule in India.

[5] In the 1930s, He represented Mohun Bagan in multiple tournaments alongside some of club's legendary players — Karuna Bhattacharya,[18] Syed Abdus Samad,[19][20] Umapati Kumar,[21] Sanmatha Dutta, Bimal Mukherjee, and Satu Chowdhury.

[24] After gaining independence from Great Britain in 1947, India sent a football team to the 1948 Summer Olympics in London, England.

[25][26][27] Chatterjee became head coach of India and he had prepared the team that defeated Department Store XI 15–0 on 13 July, and Metropolitan Police F.C.

[33][34][35] His team was having some legendary footballers of the country, captain Talimeren Ao,[36][37] Sailen Manna,[38][39] Sheoo Mewalal,[40][41] Mahabir Prasad,[42][43] and Ahmed Khan.

[44][45] After the tournament, Indian footballers' bravery and brilliance in bare feet, earned them admiration of Princess Margaret, younger sister of Queen Elizabeth II.

[46][47][48] India later went on to play few friendly matches in their Nederlands tour, where they went down to Sparta Rotterdam, but managed to win 5–1 against Ajax Amsterdam.

India won title as few new faces like Amal Dutta,[51] Anthony Patrick, and Chandan Singh Rawat.