The 1957–58 season was Middlesbrough's 75th year in existence and 4th consecutive season in the Division Two. Also the club competed in the FA Cup.
In his fourth season as manager Bob Dennison took off Boro to the 7th place nine points below promotion to Division One. Forward Brian Clough repeated another great performance with 41 goals scored −40 in Division Two just 3 below topscorer T.Johnston (Leyton Orient/Blackburn Rovers)- forming a brilliant partnership with Alan Peacock now in his first season as starter.[1] Dennison reinfored the midfield with Holliday as left winger, meanwhile McLean retained his position as right winger providing the duo a lot of assists. [2] As central midfielders, Harris and Burbeck completed a decent campaign, on the contrary the defensive line was chaotic -even with the arrival of central back Brian Phillips- allowing a lot of goals against both Goalkeepers Taylor and Million. [3] Also, the squad reached the FA Cup fourth round being eliminated by Stoke City.[4]
Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.