The 1994 – 1995 premiership season proved to be a debacle for Ipswich Town as they finished the campaign in rock bottom position of the premier league, in a season that included suffering heavy 9-0 defeat against Manchester United. They endured little luck in the cup competitions, suffering defeat in the second round of the league cup against Bolton and an embarrassing 2-1 defeat against Wrexham in the third round of the FA Cup.
Ipswich narrowly missed out on a play off birth the following season as they finished seventh place in the first division, their league cup campaign was ended in the second phase by Stockport County and their FA cup campaign terminated in the fifth round as they suffered defeat against top flight outfit, Aston Villa.
The 1996 – 1997 season was most notable for the emergence of new Ipswich teenage prodigy, Kieron Dyer and goal keeper Richard Wright at the club. Town managed to reach a play off position however could not surge past the final of the play offs in to the premiership.
Richard Naylor was Ipswich’s finest player during the 1997 – 1998 league campaign as Town finished off in a decent fifth place at the end of the season once again failing to make the grade in the play offs. They enjoyed a fine run in the league cup, reaching the quarter finals of the competition, suffering defeat against Chelsea on penalties after putting on a heroic performance against the London club.