The 1990-91 campaign proved to be a difficult one for Portsmouth, they were poor through out the season in the league as they only managed to finish the season off in 17th position, however they had a decent run in the FA Cup that was ended by eventually winners, Tottenham, they lost 2-1 at Fratton Park. They suffered defeat to another top flight club in the league cup, losing 3-2 against Chelsea.
The 1991-92 season proved to be a very successful season for Portsmouth. They had a decent league campaign, where they finished off the season in a respectable 9th position. It was the FA cup which they were most successful in, they had their best run since 1949 as they reached the semi finals. They lost out against the eventual winners, Liverpool on penalties, after forcing the match into a replay and keeping the score line level after extra time. They were knocked out of the league cup, once again by the eventual winners, Man United, losing 3-1 in the third round.
The 1992-93 season was a huge season for Guy Whittingham and the Portsmouth football club. Pompey were outstanding in the league and were unlucky not to be promoted as they finished the season off in third place. Their star striker, Guy Whittingham was largely the reason due to success, he scored an incredible 42 league goals during the season, the highest amount scored in the league during the 1990’s for any club in the English football league. In total he scored 48 times in all competitions, the most prolific goal scorer in a single season since Steve Bull of Wolves.
The 1993-94 season saw a gradual decline in Portsmouth’s fortunes, they finished the season off in a disappointing 17th position, only winning 14 of their 46 matches. They had a good run in the league cup however, only losing to eventual league champions, Manchester united, 1-0 in the quarter finals.