In their first season back playing in the second tier of English football, Ipswich Town narrowly missed out on a play off position as they finished the campaign off in seventh position. They reached the second round of the UEFA Cup as they suffered defeat against Slovan Liberec in the second phase of the cup competition.
The 2003 – 2004 season saw Ipswich finish off the campaign in an impressive fifth position and were unfortunate not to gain promotion in to the premiership via the play offs as they crashed out of the play off semi finals. They reached the fourth round of the FA Cup however suffered a 2-1 defeat against Sunderland in the competition.
The 2004 – 2005 season saw the emergence of young striker Darren Bent, who went ton to score 19 goals for the club during that season, a year that Ipswich finished in third position, narrowly missing out on promotion via the play offs. Fabian Wilnis and Darren Currie were in fine form for Town as they swept the championship.
Darren Bent left Ipswich at the end of the 2004 – 05 season leaving for Charlton Athletic in a deal believed to be worth £2.7 million.
Ipswich suffered a poor campaign during the 2005 – 2006 league season as they could only manage to finish in a disappointing 15th place and worse was to come in the League cup as they crashed out in the first round suffering a humiliating defeat against Yeovil Town.
Jim Magilton was installed as the new manager of Ipswich Town for the start of the 2006 – 2007 season after the departure of Joe Royle.