The 1960-65 era proved to be a debacle for all Pompey fans; their club were poor and were even demoted to the third division.
The 1960-61 campaign, was a disaster, they finished off the season in 21st position, fortunate to avoid relegation, despite their awful performances. Their first appearance in the league cup was credible; they reached the last eight, only to be humiliated 3-0 against Rotherham. They suffered an early exit in the FA Cup, losing to Peterborough. Their first ever campaign in the third division the following year was a success, they topped the league by the end of the season. They suffered an early exit form the FA Cup, losing 3-0 against Crystal Palace. Portsmouth’s season back in the second tier of English football was far from impressive, they struggled through out the season and only managed a 15th position ending. They were knocked out of the FA Cup and League Cup in the forth rounds, losing to Sunderland and Coventry City respectively.
A significant improvement in league form was seen the following season as they finished ninth in the second division. They reached the forth round of the league cup however they lost 3-2 against Notts County. The 1964-65 campaign produced a poor performance by Pompey, they were woeful in the league, fortunate to avoid relegation in 20th place. They suffered elimination in the cups, in the third round, losing to Wolves and Northampton respectively.