The 1985-1986 season proved to be the last one for Ian Porterfield in charge at the club. In what proved to be a successful campaign, Sheffield United finished the season off in a very respectable seventh place, narrowly missing out on a play off place. They lost against Derby County 1-0 in the forth round of the FA Cup.
The 1986-87 campaign saw the arrival of new manager Billy McEwan and the club faired well during the 1986-1987 season as they finished it off in a very respectable ninth place. They crashed out of the league cup in the third round, suffering a 3-1 defeat against future finalists, Oxford United.
The 1987-1988 season proved to be an unmitigated disaster for the club as they plummeted down the second division, painfully finishing the campaign off in 21st place, in turn demoting the club to the third division. They also crashed out of the FA Cup in the forth round, suffering defeat against Portsmouth FC. Billy McEwan departed the club at the end of the campaign and he was replaced by former Wimbledon manager, Dave Bassett. Bassett went on to sign many key players for the club, including Billy Whitehurst, Mark Morris, Colin Hill and Tony Agana, the latter signing for £45,000 and ended up being the clubs top goal scorer during the 1988-1989 season. The blades earned automatic promotion back in to the second division by the end of the 1988-1989 season. Bassett proved to be one of the greatest managers in the game the following season as he mastered a back to back promotion by the end of the 1989-1990 season. The Blades finished the campaign off in second place, just behind Leeds United and earned promotion back into the top flight for the first time in 14 years. Sheffield United enjoyed a great run in the FA Cup, reaching the quarter finals only suffering defeat against eventual FA Cup winners, Manchester United, losing the clash 1-0.
The 1989-90 Sheffield United side included players like, David Barnes, Bob Booker, Paul Stancliffe, Carl Bradshaw, Ian Bryson, John Gannon, Paul Stancliffe and most importantly, Brain Deane, who proved to be the clubs best player during the 1989-90 season and was prolific in front of goal and went on to become a favourite with the Sheffield United supporters.