Ellis Stuttard took charge at Plymouth between 1961 and 1963 and he took Plymouth to the brink of promotion in to the first division as they finished the 1961 – 1962 season off in fifth position in the second division. Andy Beattie took charge at the club during the 1963 – 1964 season and saw his side finish off in a disappointing 20th position. Malcolm Allison took charge during the 1964 – 1965 season as the Pilgrims made a slight improvement, finishing the campaign of fin 15th position.
Derek Ufton took charge in 1965 and went on to spend three years in charge at the club, as they gradually slumped into the second division, they stared relegation by the face towards the 1967 – 1968 campaign as they finished it off in 22nd position, in turn relegating the cub to third division football. Billy Bingham took charge at the club in 1968 and nearly guided the Pilgrims to promotion at the end of the 1968 – 1969 season as they finished it off in fifth position.