Wheater experienced his best season of football during the 2007–08 season, starting as a regular for Gareth Southgate's side and becoming an imposing force at the back. Wheater scored four goals in all competitions during his 2007–08 breakthrough season. At the end of the year, he won the North East Football Writers' Association Young Player of the Year and Player of the Year awards for his exploits. Unfortunately, Middlesbrough were relegated at the end of the 2008–09 season, but Wheater decided to stay to try to help the club regain promotion.