Coventry were challenging for the Southern League title at Christmas and went on to reach the FA Cup quarter final, beating top-flight teams Preston and Nottingham Forest before losing to Everton.
[76] They made several expensive signings, including full-back Terry Springthorpe and striker Tommy Briggs, but these players had no impact at the club and a run of poor performance in the new year ended their promotion hopes.
The club did not achieve promotion that season, with a fourth-place finish, but had their most successful run in the FA Cup for many years, beating Bournemouth, Millwall, Lincoln, Portsmouth, and Sunderland en route to a quarter-final defeat by Manchester United.
City appeared to have missed out on promotion when they lost 2–0 at Peterborough in April, but they were saved by some poor results for their rivals and a winner by the returning Hudson in a final-day victory over Colchester, giving them the championship.
New signings during this time included goalkeeper Bill Glazier and striker Ian Gibson, while local player and future manager, Bobby Gould, began to appear regularly in the side.
The tactic meant City conceded more goals than previously, but with Yorath and Barry Powell as anchors in midfield, Hutchison and new signing Ray Graydon on the wings, and Wallace and Mick Ferguson as strikers, the attack were more than able to compensate.
A late-season run of thirteen games with only one defeat and progress to the FA Cup quarter finals, inspired by former England captain Gerry Francis, left supporters feeling more optimistic by the end of the season.
The new recruits included members of the future cup-winning side, Dave Bennett, Michael Gynn and Trevor Peake, as well as Micky Adams, Sam Allardyce and Stuart Pearce, the last of whom joined from non-league Wealdstone a few months into the season.
[159] Steve Ogrizovic, who would go on to break the club's appearance record,[160] joined from Shrewsbury, Brian Kilcline moved from Notts County, and England-international Cyrille Regis switched from West Bromwich Albion.
[168] The home side played better in the first half but Coventry withstood the pressure and once again took the game 1–0, Michael Gynn scoring on the rebound after David Phillips had failed to convert a Nick Pickering cross in the 72nd minute.
Key players in Coventry City's FA Cup winning team included goalkeeper Steve Ogrizovic, defender and captain Brian Kilcline, midfielders Dave Bennett and Lloyd McGrath, and strikers Cyrille Regis and Keith Houchen, who scored the famous diving header.
[177] Coventry replaced a number of players during the 1989 close-season, buying defender Peter Billing and acquiring Liverpool's Kevin MacDonald on a free transfer, with David Phillips and Steve Sedgley leaving the club.
December injuries to Dublin and David Busst led to a poor run of results, culminating in FA Cup defeat to Norwich and supporters quickly turned against Phil Neal.
After making a reasonable start, the team suffered their worst run in the top flight, playing fourteen league games without a win and by early December, City were bottom of the table.
This decision proved a very unpopular one with the majority of the club's fans, as Black (who was popular and had been doing a good job with relatively limited resources) had been seen to have been ousted for a 'big name' whose management style was perceived as 'old school' and not fitting with the modern game.
Adams helped the Sky Blues stay clear of the Championship drop zone in their final season at Highfield Road before relocating to a new 32,600-seat stadium at Foleshill (later named the Ricoh Arena as part of a sponsorship deal).
Micky Adams was expected to challenge for a play-off position in the 2006–07 season but was relieved of his duties in January 2007 after a string of poor results and an embarrassing FA Cup exit at the hands of lower league Bristol City, bringing to an end his two-year reign.
Whilst still distinctly 'work in progress', Dowie's team selections looked defensively better-organised than his predecessor's, with more attention paid to solid midfield possession, a more fluid counter-attacking strategy and some shrewd new signings.
They eventually succumbed in this competition after a 2–1 loss to the Premiership's West Ham United in a game the Sky Blues completely dominated (West Ham's goals came from a cruel deflection and a highly fortunate goal deep into injury time), thus missing out on a lucrative place in the quarter-finals.Following a highly successful start to the season, Dowie was named "Manager of the Month" for August 2007, having secured top position after the first four league games and two successive League Cup wins.
On 6 October 2007, Paul Fletcher tendered his resignation in the wake of numerous takeover bids being priced out of the market, leaving both Operation Premiership and the long-term financial future of the club up in the air.
[216] Faced with large losses, SISU had responded by selling many of the club's top stars such as Danny Fox and Scott Dann, while failing to agree new terms with out-of-contract players including Marlon King and goalkeeper Keiren Westwood.
This triggered another 10-point deduction, but the Football League allowed the club to continue playing by agreeing to transfer its golden share to the administrator's preferred bidder, Otium Entertainment Group,[233] a company majority owned by SISU.
[253][251] Significant transfers included the departure of star midfielder James Maddison to Norwich, and the arrival of former England international Joe Cole from Aston Villa, initially on loan and later on a full-time deal,[251] although he departed for American club Tampa Bay Rowdies at the end of the season.
In early June, with talks unresolved and faced with the threat of expulsion from the league over its lack of a confirmed home for 2018–19, the club announced that it would once again leave Coventry to commence a ground share with Birmingham City at their St Andrew's stadium.
[283] The club made a very positive start to the 2021–22 season and gave themselves a great chance of achieving a Play-Off spot, with the goals of Swedish international striker Viktor Gyökeres proving pivotal in their push.
After the club endured a stop/start beginning to the 2022–23 season thanks to the aforementioned postponements due to the pitch issues at the CBS Arena they found themselves rock bottom of the League in October 2022, albeit having played far less games than everybody else.
On 27 January 2023, just two weeks after his majority takeover was ratified by the EFL, Doug King increased his ownership stake in Coventry City buying out the remaining 15% of SISU's shares making him the clubs sole owner.
[290] In the summer of 2023 and following their failure to seal promotion to the Premier League star players Gustavo Hamer and Viktor Gyökeres departed The Sky Blues, the latter for a club record outgoing fee.
[291][292] Robins used the funds generated from the Hamer and Gyökeres sales to revamp his side including breaking the club's inbound transfer record on American international striker Haji Wright.
Coventry were the unfortunate victims of one of the most controversial[citation needed] offside decisions in FA Cup history when Victor Torp’s last minute ‘winner’ was ruled out by a very small length.