Jack McKenna is a midfielder who progressed through the Rovers youth ranks, breaking into the first team squad at the start of the 2009–10 season at the same time as Eliot Richards, Dan Cayford, Mark Cooper, Neikell Plummer, George Booth, Steve Kingdon and Ollie Clarke. He never make a first team appearance for The Gas, although he was an unused substitute in one game, a 2–1 defeat at Brighton & Hove Albion in April 2010. After a two-month long loan with Chippenham Town early in 2011 he was released by The Pirates on 1 April that year, enabling him to sign for Frome Town.