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Ahead of the 2018–19 season, Ochieng signed for newly promoted National League club Braintree Town. Ochieng made five appearances for the Iron before joining Welwyn Garden City on 28 March 2019. He joined Wingate & Finchley for the 2019–20 season. On the 30th January 2020, it was announced by Wingate & Finchley that Ochieng had been sold for an undisclosed fee to League of Ireland Premier Division side Cork City, returning to professional football following 31 appearances for the club. The following day, Cork officially announced the signing of Ochieng.

Ochieng, whose parents were born in Kenya, was called up by the Kenya national football team for their 2019 Africa Cup of Nations qualifier against Sierra Leone in November 2018, but the match was later cancelled. He instead made his debut for Kenya U23 against Mauritius on 14 November 2018 in 2019 Africa U-23 Cup of Nations qualification.

Ochieng made his first-team debut on 8 November 2016 as an 81st-minute substitute for Žan Benedičič in Orient's 1–0 away defeat to Brighton & Hove Albion U23 in the EFL Trophy. He signed his first professional contract in December. He made his League Two debut on 25 March 2017 as an 81st-minute substitute for Nigel Atangana in Orient's 3–0 defeat away to Crawley Town.

He was born to Kenyan parents, Sam and Perez Ochieng, in Redbridge, London. He was raised in Ilford and attended St Aubyn's School in Woodford Green and later Forest School in Walthamstow. He started his career with local junior side Buckhurst Hill before being spotted and signed by the youth team at West Ham United in 2009. He signed a two-year scholarship with Leyton Orient in 2015.

Henry Oliver Ochieng (born 11 November 1998) is an English-born Kenyan professional footballer who plays as a midfielder for Cork City. Ochieng was a part of the West Ham United academy.