Bob Dennison took Boro to the brink of the top flight by the end of the 1959-60 season as Middlesbrough finished the season off in fifth place. They could only manage to reach the third round of the FA Cup, losing against Manchester united 3-0.
The 1961-62 campaign saw a decline in their fortunes as they finished the season off in 12th place, they did however embark on a fine run in the FA Cup, reaching the fifth round, losing against Blackburn Rovers. Richard (Dickie) Robinson and Brian Clough left the club at the end of the season.
Denninson’s last season in charge at the club saw the club agonizingly miss out on the top flight ass they finished the season off in forth place. Boron narrowly missed out on the fifth round of the FA Cup as they lost against Leeds United. The following two seasons saw Boro’s fortunes gradually deteriorate as they finished the campaigns off in 10th and 17th position respectively. Raich Carter was installed as the new manager at the end of the 1962-63 season. Boro reached the fifth round of the FA Cup, losing 3-0 against Leicester City.