[3][4][5] The club also roped in the services of Odisha winger Nandhakumar Sekar and Chennaiyin midfielder Edwin Sydney Vanspaul for the season.

[12] On 12 June, East Bengal announced the signing of Spanish midfielder Borja Herrera on a one-year contract in a free transfer.

[15] On 19 June, the club announced the signings of three players – Edwin Sydney Vanspaul, Harmanjot Singh Khabra and Mandar Rao Dessai.

[16] East Bengal appointed former Indian Super League winner Carles Cuadrat as the new head coach for the club on a two-year contract.

[43] The club also roped in three more Spaniards into the backroom – Goalkeeper coach Javier Pinillos, Physiotherapist Senen Alvarez and Sports Scientist Albert Martinez Bernat.

[49] On 12 August, East Bengal faced their arch—rivals Mohun Bagan SG in the Kolkata Derby fixture at the Salt Lake Stadium and managed a 1–0 win courtesy of a solitary goal from Nandhakumar Sekar in the second half.

[50][51] On 16 August, East Bengal defeated Punjab 1–0 at the Kishore Bharati Krirangan to secure the top spot in the group and qualify for the quarterfinals.

Jordan Elsey scored for East Bengal in the very first minute but Gokulam Kerala equalized in the second half courtesy of a goal from Aminou Bouba.

[54] On 3 September, East Bengal faced Mohun Bagan SG in the final at the Salt Lake Stadium and suffered a 0–1 defeat to finish runners-up of the tournament.

Hitesh Sharma put Hyderabad ahead but Cleiton Silva scored twice including a stoppage-time freekick winner to complete the comeback as East Bengal secured the victory.

[61] On 25 November, East Bengal faced Chennaiyin away at the Jawaharlal Nehru Stadium and drew 1–1, to end their three-match defeat streak.

[73] On 24 January, East Bengal faced Group B winners Jamshedpur in the semi-finals and won 2–0 with goals from Hijazi Maher and Javier Siverio as they entered the final for the second time, after 2018.

However, captain Cleiton Silva scored the winner in the 110th minute as East Bengal secured a 3–2 victory to become the champions and lift a major trophy after twelve years.

[47] In the opening match on 13 July, East Bengal faced ASOS Raibow at the Kishore Bharati Krirangan and were held onto a goalless draw to start their campaign.

[84] On 9 August, East Bengal defeated Railway FC 2–0 with goals from Aman C. K. and Nishu Kumar to earn their fifth win of the campaign.

[85] On 14 August, East Bengal defeated Police AC 2–1 with goals from Avishek Kunjam and P. V. Vishnu to grab their sixth win of the campaign.

[86] On 19 August, East Bengal defeated Aryan 2–0 with goals from Jesin TK and Aman C. K. as they grabbed their seventh win of the campaign.

[88] on 7 September, East Bengal faced George Telegraph in the last match of the first phase and won 4–0 to finish top of the group with 30 points and entered into the Super–six round.