Wark signed for Middlesbrough, the first club to show "a definite interest" in him, on a two-year contract, moving back to play in the centre of defence. He made regular appearances and helped the team to seventh place by the end of the season and qualification for the Second Division play-offs. Following a 1–1 draw with Notts County at Ayresome Park, Wark was informed by manager Colin Todd that he would not be selected for the second leg. Wark was outraged; Middlesbrough lost the second leg 1–0. Todd departed from the club and was replaced by Lennie Lawrence, who insisted that all players live "within an hour of Ayresome Park". Wark was still living in Ipswich at the time and following a "sensible agreement" with Lawrence, Wark's contract was terminated and he became a free agent again.