The 1958–59 season was Middlesbrough's 76th year in existence and 5th consecutive season in the Division Two. Also the club competed in the FA Cup.
In his fifth season as manager Bob Dennison took off Boro to the 13th place a massive twenty points below promotion to Division One. Forward Brian Clough scored 43 goals being Division Two topscorer with another brilliant partnership among Alan Peacock. [1] After the departure of Jamaican Lindy Delapenha during summer, the offensive line was hit with several injuries such as Mc Lean and Fitzsimons, forcing Dennison and the staff coach to line up Scottish Forward Willie Fernie[2] who delivered a decent performance after arriving from the Scot squad playing the 1958 FIFA World Cup. [3] In spite of a premier class offensive line, Boro again collapsed due to a weak defensive line despite the arrival of Ray Yeoman[4] and future starter Left-back Defender Mick McNeil[5] allowing a lot of goals against both Goalkeepers Taylor and Million. [6] Also, the squad reached the FA Cup third round being eliminated by Birmingham City.[7]
Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.