Bobby Ferguson could not turn around what had proved to be a disappointing two pervious years at Ipswich Town football club during the 1985 – 1986 league campaign as they finished the season off in 20th position, in turn relegating the club in to the second division, a place they had not been in for 17 years. Their first season back in the second division saw then nearly gain promotion back in to the top flight via the play offs, however their fifth place finish was not enough to see them through.
Johnny Duncan took charge at the club in 1987 and Ipswich’s league fortunes began to slum as the 1987 – 88 campaign saw Town only managing an eighth place finish. For much of their time in the late 1980’s, Ipswich were hovering around the top ten of the second division and could only manage an eighth position finish at the end of the 1988 -89 season and a ninth place finish at the end of the 1989 – 90 campaign.
The Ipswich Town football side of the 1989 – 1990 season included Craig Forrest, Frank Yallop, Neil Thompson, Brian Gayle, David Lowe, David Linighan, John Wark, Simon Milton, Andy Kiwomya and Jason Dozzell.