Coventry City have come close to re-joining the Premier League on a number of occasions in the past few seasons, with their semi-final play-off defeat to Sunderland the latest agonising near miss.
Frank Lampard and Coventry may now be in the market for a number of signings to ensure this heartbreak does not happen in the 2025/26 season.
In order to do this, it may mean splashing the cash and breaking their previous transfer record.
Coventry have had some quality players over the years and will need to bring in a few more to get them over the line.
However, who are the five most expensive transfers to ever join the Sky Blues?
The five most expensive signings made by Coventry City
5. Ellis Simms – £6 million
In the summer of 2023, Ellis Simms joined Coventry City from Everton after he struggled to make an impact throughout his time at Goodison Park.
Simms had impressed in the Championship at Sunderland, earning his return to Everton, but he struggled to score in the top flight.
He returned to the Championship when he signed for Coventry City, and he has thrived in the sky-blue shirt, scoring 26 goals in 99 games.
Fans will be hopeful he can find his early form, as he struggled last season in front of goal; however, he has shown he can do it at this level, and he should help in the club’s promotion push.
4. Lee Hughes – £6.5 million
To call Lee Hughes a journeyman striker would be considered an understatement, as he played for over 15 clubs, with Coventry being his third professional club.
Hughes only lasted a year at Coventry, after he signed for the club in the summer of 2001, under Gordon Strachan.
He was signed to help the club return to the Premier League, and while he would finish as top goal scorer in his one season at the club, it would not be enough to see Coventry return to the Premier League, as they finished outside the play-offs in 2002.
He would re-join West Brom, the club Coventry signed him from, after only playing 44 matches, scoring a total of 15 goals.
3. Robbie Keane – £7.8 million
The Republic of Ireland legend joined the club from Wolves for a reported fee of £7.8 million in 1999.
Robbie Keane had impressed at the Championship level with Wolves, scoring 29 goals in 87 games; however, still at the age of 19, there were concerns the high fee paid for the teenager would be a waste if he struggled to adapt to the Premier League.
These were soon rubbished as he took to life in the English top flight like a duck to water, scoring 12 goals and helping keep Coventry in the division.
His time at the club would be brief, as he departed for Inter Milan the next season for a fee of £13 million, a significant profit on Coventry’s investment.
2. Haji Wright – £7.8 million
Haji Wright was brought in shortly after the acquisition of Simms, showing the significant investment the club were willing to make to bring about a future back in the Premier League.
Wright has at times shown exactly why Coventry splashed the cash on him, as he has flashes of brilliance; however, he has struggled for consistency at times.
He has also been rumoured to potentially be making an exit from Coventry this summer to return to Turkey, yet nothing firm has materialised.
At present fans will be hopeful he can find some form and push the club back to the English top flight, building on the 31 goals he has scored across 79 matches.
1. Craig Bellamy – £8 million
The most expensive signing Coventry have ever made comes in the figure of Craig Bellamy, when he opted to join the club from Norwich City in the summer of 2000.
Coventry had just been blessed with money from the sale of Robbie Keane and also needed to replace the Irishman, with Bellamy being viewed as that man.
Bellamy would not be able to help the club stave off relegation in 2001; despite finishing with the joint highest league goals that campaign for the club, he struggled.
He spoke about how he found it difficult at Coventry, never settling and wishing he had joined Newcastle United.
Bellamy got his wish upon Coventry’s relegation to the Championship, as he joined Newcastle in the summer of 2001 as the club looked to reduce their wage bill.
