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.
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