The 1965-66 campaign proved to be a debacle for Boro as they stumbled in the second division to a poor 21st place finish, in turn relegating the club to the third division for the first time in the clubs history. It proved to be Raich Carter’s last season in charge at the club and finishing in the third round of the FA Cup capped off a miserable season for the club. Stan Anderson took charge at the club the following year as Middlesbrough were emphatic in the third division as they cruised into second place, in turn earning the side an immediate automatic promotion to the second division. Anderson and Boro nearly struck gold the following season as they were outstanding through out the campaign and nearly clinched a back to back promotion. They finished the 1967-68 season off in sixth place, close to an automatic promotion place.
Willie Maddren was in outstanding form for Boro during the 1968-69 season and his great play rubbed off in the team as Boro finished the season off in an incredible forth position, once again coming close to automatic promotion.
The 1969-70 season was another delightful campaign for Boro, once again coming agonisingly close to securing automatic promotion to the top flight as they finished off strongly in forth position. They embarked on a great run in the FA Cup that saw the side reach the quarter finals of the competition, narrowly losing against the mighty Manchester united by 2-1.