Charlton struggled during the 1994-95 season, a 15th place finish was a sour product for the Valliants by the end of the season. David Whyte permanently moved to the club at the start of the season and it proved to be an inspirational one. They could not progress far in the FA Cup, crashing out of the competition in the third round, suffering a 3-0 humiliation against premiership club, Manchester United.
Welsh international, John Robinson, was inspirational for Charlton during the 1995-96 campaign, the addicks were in fine form through out the season, strong in the league, earning a play off birth from a sixth position finish, however the play offs proved to be unfruitful for the club. They also put on a decent show in the FA Cup, reaching the fifth round, facing the future finalists, Liverpool, they were unfortunate to lose the tie 2-1. The addicks lost in the third round of the league cup, losing against Wolves after extra time.
The 1996-97 season witnessed a downturn in Charlton’s fortunes, struggling in the league to a 15th position finish. The 96-97 season witnessed the debut of their rising young star Kevin Lisbie, one of the plus points coming from a disappointing campaign. The addicks narrowly missed out on the forth round of the FA Cup, losing 2-1 against Newcastle United 2-1 after extra time. They met tough opposition in the third round of the league cup, an encounter with Liverpool proved to be more of an embarrassment as the addicks crashed out of the match losing the game 4-1.
Improvement was essential during the 97-98 season and Charlton witnessed what they went in search of, a forth position finish, earned the club a play off place. They were emphatic in the play offs, winning the competition, with the reward being a lucrative position in the top flight. Alan Curbishley became a hero at Charlton and got the club prepared for premiership football. The addicks reached the forth round of the FA Cup, losing 3-0 against Wolves.