He formed a crucial part of the club's academy team which would go on to win the AIFF U-15 & U-16 Youth League titles two consecutive years.

[8] He was promoted to the senior team by newly appointed Blasters coach Eelco Schattorie for the 2019–20 Indian Super League.

He played 82 minutes in the defensive midfield position before being substituted by Sahal Abdul Samad, as Kerala Blasters beat ATK 2–1 at home.

[11] On 20 December, he scored his first goal in the Indian Super League as well as for the Blasters by coming in as a substitute for Rohit Kumar in the 46th minute against East Bengal during the stoppage time, taking the game to a 1–1 draw.

[12][13] On 27 December 2020, he had a good performance against Hyderabad, as Blasters registered their first win of the season by 2–0, where Jeakson won the Man of the Match award.

[19][20] He formed a solid partnership with Puitea in the midfield and helped the Blasters to reach the finals, which they lost to Hyderabad on penalties.

[26] In the first away league game of the season against Mumbai City on 8 October, Jeakson was substituted in the beginning of second half after suffering a shoulder injury following a challenge on Greg Stewart.

On 20 October, the Blasters' assistant coach Frank Dauwen, during the pre-match press conference said that Jeakson needs surgery and will be out of action for two to three months.

[34] In March 2022, he was again included in the national squad by coach Igor Štimac ahead of India's two friendly matches against Bahrain and Belarus.

[35] On 14 June, Jeakson provided an assist for Sunil Chhetri's second goal against Hong Kong in the 2023 AFC Asian Cup qualification, which India won 4–0.