The 1985-86 season proved to be Willie Maddrens last season in charge at the club as Middlesbrough embarked on an awful campaign that saw the side finish off in 21st position, in turn relegating the club to the third division. The emergence of new players, Gary Pallister and Stephen Pears was the few pluses coming from a miserable campaign that also saw Boro reach the third round of the FA Cup, losing against Southampton 3-1.
Bruce Rioch was the man who took Boro straight back up the following season as they were emphatic in the third division, finishing the season off in second place. They were knocked out of the FA Cup in the third round, losing against Preston North End. Alan Kernaghan and Colin Cooper were consistent through out the campaign for the side. Rioch’s honeymoon period as manager of the club was lengthened dramatically the following season as Boro shined in the second tier of English football. Middlesbrough embarked on a heroic campaign that saw the side earn a back to back promotion in to the top flight as they finished the season off in third place. They were knocked out in the forth round of the FA Cup, narrowly losing 2-1 against Everton FC.

Rioch brought in Peter Davenport into the Boro side during the 1988-89 season, buying the player from Manchester united for £700,000 in November 1988. Boro’s stay in the top flight was short lived as they could not survive the relegation battle and only narrowly missed out on survival, finishing the campaign off in 18th position. Boro saw the departure of their star player, Gary Pallister at the end of the season, leaving for Man United for a fee of £2,400,000. The 1989-90 season proved to be a debacle for Middlesbrough as they had an awful league campaign in the second division that nearly saws the side relegated once again. They finished a miserable campaign off in 21st place as they only won 13 of their matches during the season. The 1989-90 Middlesbrough side included the likes of Tony Mowbray, Trevor Putney, Stuart Ripley, Simon Coleman, Gary Parkinson and Stephen Pears.