The 1999 – 2000 season proved to be a resounding success for Ipswich Town as they finally gained promotion in to the premiership in what was their fourth attempt.
They gained promotion via the playoffs as they finished off the season in third position. Titus Bramble was in fine form for the Tractor men as they found promotion. They reached the second round of the league cup, crashing out after suffering defeat against Crewe Alexandra.
Their first season back in the premiership proved to be a fantastic year for the club as they were emphatic in the top flight. They finished the campaign off in fifth position, which in turn landed them a place in the UEFA Cup. Malcolm Christie was in fine form for the club and George Burley had performed heroics in guiding the club too such a high finish. They were also convincing in the league cup that season as they reached the semi finals of the competition only suffering defeat against Birmingham city in the last four of the competition.
Ipswich could not sustain their fine form the following season as they crashed right down the league and finished the season off in 18th position, in turn relegating the club back in to the first division, two years after finding promotion. They crashed out of the FA Cup and league cup in the fourth round losing against Manchester City and Newcastle United respectively.
Ipswich had many fine players at their disposal including Marcus Bent and Darren Ambrose.