Jermaine signed for Woking in December 2021 after leaving neighbours Aldershot Town the previous summer. The centre midfielder made his senior debut in November 2012, making the first of 97 appearances for Peterborough, 75 of which came in League One. He scored eight goals for the Posh, including six in 2015/16, but two separate knee injuries limited his progress. After a loan spell with Doncaster Rovers, he joined Bradford City, where he spent 18 months, playing in both League One and Two. He joined the Shots in December 2020, playing 34 times in all competitions, scoring four goals - including two against the Cards on Boxing Day. His season was ended early by a broken leg, but after recovering, he joins the Cards looking to continue his good form in the National League.