Coventry City will always have Ipswich Town envy – Tractor Boys stole their millions | OneFootball

Coventry City will regret the sale of Conor Chaplin to Barnsley, especially after his impressive stint at Ipswich Town.

Back in the summer of 2019, Coventry City opted to cash in on key attacker Conor Chaplin to Barnsley, but it is perhaps a decision that the Sky Blues look back on now with regret.

A couple of years later, Ipswich Town completed the signing of Chaplin from Barnsley for £750,000, in a summer transfer window that saw the Tractor Boys shell out some major fees to try and return to the Championship under the management of Paul Cook.

A lot of the signings that they made over that window didn’t come off and a lot of players had to be moved on, but Chaplin is a player that, already with a good reputation, even went on to improve at Portman Road.

Coventry and Ipswich are now both rivals in the second-tier once again in the 25/26 season, with Chaplin having returned to Portsmouth on a season-long loan deal, but there will still be some regret from Coventry, from a footballing perspective as well as a financial one, that they didn’t keep hold of the attacking midfielder.

Coventry City could have kicked on quicker with Conor Chaplin

During the extremely impressive managerial stint of Mark Robins, Coventry were looking to build on an excellent eighth-placed finish in their first season back in League One ahead of the 19/20 campaign.

They had risen from League Two to the third tier under Robins at the first time of asking, but Chaplin had only ever played a smaller part in that rise, scoring eight goals in 32 appearances for the club after his move from Pompey in 2018.

Despite that, Barnsley were still tempted to purchase the then 22-year-old for a fee that could have reportedly risen to over £1 million – and it appeared to be a good deal at the time.

It appeared to be an even more impressive sale two years later when, despite having notched double figures in the Championship in his first season with the Tykes, Chaplin was then sold to Ipswich Town in the summer of 2021 for a fee of £750,000, and back down to League One.

Reuniting with Paul Cook, with whom he had played under at Pompey, Chaplin showed some signs, but his better performances did come in the second-half of the campaign after the appointment of Kieran McKenna; and it is with McKenna at Ipswich whereby Chaplin made Coventry, and Barnsley, regret their transfer decision-making process.

Conor Chaplin became Ipswich Town star under Kieran McKenna

Chaplin's first season in Suffolk was a modest one, bagging just nine goals in 39 league outings, as Ipswich finished 11th in League One.

However, Ipswich would win automatic promotion to the Championship in the 2022/23 League One season, amassing 98 points, and Chaplin was immense for the Tractor Boys.

Playing as a second striker in a 3-5-2 on occasion, as well as the out-and-out striker in a 4-2-3-1 or even the attacking midfielder in that same formation, Chaplin was given the freedom to express his undoubted technical talent, whilst also showing the intelligence and energy to play in a McKenna-coached side.

He scored 26 goals in 45 League One appearances that season before then playing more of a supporting, but still extremely important, role in the Championship, scoring 13 goals and providing eight assists, as they gained an unlikely promotion to the Premier League.

In the summer of 2024, Chaplin was a player who had proven himself to be the chief creator for a Championship promotion-winning side, but also someone who could be relied upon as a major source of goals.

His value may have dipped since that time given his struggles in the top-flight and his subsequent loan exit to Portsmouth, but it would have been far higher than the fees that both Coventry and Barnsley both sold Chaplin for, let alone the influence on the footballing side of things that he could have had for both clubs.

Coventry had a very strong squad in the 2022/23 campaign, when Chaplin was hitting 26 goals in the third-tier for Ipswich, but it wouldn’t be an exaggeration to suggest he could have been their missing piece alongside Viktor Gyokeres as they missed out on winning the Championship play-off final on penalties to Luton Town.

The millions he could have made Coventry from his potential sale, had they held on to him for a few more years, are dwarfed by what he could have done by the eventual delivery of promotion that he achieved with Ipswich.