1990–91 Coventry City F.C. season

The season started poorly, with a win against a struggling Everton side the only highlight of the opening games. Under pressure to change something, and with regulars Dean Emerson and Lloyd McGrath injured, Sillett signed players from Europe to add depth to the team. Winger Zoltán Csucsánszky came from Hungary for a trial, but sustained an injury in his first game, a friendly.[7] Uruguayan José Perdomo had more success, arriving on loan from Genoa and impressing Sillett in six games for Coventry. The club were unable to sign him permanently, however.[8]

Results did not improve significantly as the autumn progressed, and morale was poor. Star striker David Speedie was dropped from the team after a run of poor performances, and by November the club were in sixteenth position.[9] In November, the club announced that Sillett was leaving his post as manager. Historians do not know if he resigned or was sacked, although he was not working due to sickness at the time and had been planning to leave at the end of the season anyway. The club appointed Terry Butcher as Sillett's replacement.[8] Butcher was still an active player for Rangers at the time, and had been captain of the England team during their World Cup semi-final against West Germany in the summer, so he arrived as player–manager and the club had to pay a transfer fee of up to £450,000 for him. His first game, at home to Liverpool, ended in a defeat.[10]

Despite success in the League Cup, Butcher had to wait more than a month before the club won a league game under his management and supporters feared that the club would be dragged into a relegation battle. Butcher bought Ray Woods from Wigan Athletic, but was forced to sell the promising young players Steve Livingstone and Tony Dobson, who both left for Blackburn Rovers. Speedie was also sold, moving to Liverpool for £675,000, following a series of sub-par performances and a poor relationship with Butcher. Butcher then signed Kenny Sansom and Stewart Robson, and the club began to record some better results,[11] recording home wins against Aston Villa, Manchester City and Chelsea, amongst others. By mid-April, with three games remaining, Coventry had moved up to ninth place in the table, but two defeats from their last three games saw them finish in sixteenth.[9]

The league season had been a contrast between excellent form at Highfield Road, where the side won ten of nineteen games and were unbeaten after the November defeat to Liverpool, and a poor away record with just one win,[11] at Sheffield United early in the season.[9] The player of the year was Kevin Gallacher, who scored eleven league goals.[12] As a player, Terry Butcher had only started seven games, six in the league, as a result of injury. Cyrille Regis played well throughout the season, but did not score heavily and was released by Coventry at the end of the season, moving to rivals Aston Villa F.C.[11]

Following defeats to lower-division and non-league opposition in the previous two seasons, Coventry faced the possibility of another upset in the third round against Wigan Athletic.[8] Wigan had some future top-flight players in their team including Peter Atherton, who later signed for Coventry, but were having a poor season, being in seventeenth place in Division Three. The first match, played at Highfield Road on 5 January 1991, ended in a 1–1 draw as Micky Gynn's opener in the 66th minute was cancelled out by a last minute equaliser by Wigan's Darren Patterson.[13] The replay at Springfield Park was four days later and was won 1–0 by Coventry courtesy of another Gynn goal.[14]

In the fourth round in late January, a few days after their defeat in the League Cup quarter final, City again drew 1–1 at home against Southampton with Alan Shearer equalising after Brian Kilcline's opener.[15] In the replay at The Dell City had eight players out through injury,[11] and lost Steve Ogrizovic after 24 minutes. Southampton went on to win 2–0.[15]

After reaching the semi-final in the 1989–90 season,[16] Coventry again performed well in the 1990–91 Football League Cup, also known as the Rumbelow's Cup. The campaign began in September with a two-legged second-round tie against Bolton Wanderers, in which City won both their home and away games by scores of 4–2 and 3–2 respectively. In the third round, on 31 October, they played at home to Hull City. The visitors dominated the first half but were unable to score, and then suffered the set-back of losing former Coventry player Dave Bamber. Coventry improved after half-time, and won the game 3–0 with goals from Speedie, Livingstone and Regis.[15]

In the fourth round on 28 November,[15] Coventry faced Nottingham Forest, in Butcher's third match as manager. Forest had won the tournament in both of the previous two seasons, beating City on each occasion, and started the match as favourites. After 35 minutes, Coventry had moved into a 4–0 lead with Gallacher claiming a hat-trick and Steve Livingstone also scoring. Forest responded, however, and Nigel Clough, son of manager Brian Clough, stunned Highfield Road with a hat-trick of his own, scored in just seven minutes and leaving the score 4–3 at half time.[17] Forest levelled the match through a Garry Parker goal after half-time, but Livingstone's goal with half an hour remaining won the game for Coventry by a 5–4 scoreline.[18]

City had to wait almost two months for their next match in the competition, the quarter-final tie at home to Sheffield Wednesday of the Second Division. Coventry created few chances in the game, with player-manager Terry Butcher sustaining an injury as well, and Nigel Pearson's 9th-minute goal was enough to win the tie.[15]

Source:[20]

Source:[21][7][11]

Transfers in: £225,000

Transfers out: £750,000

Total spending: £525,000