7-figure Coventry City transfer may never work out - Preston North End will be left very confused | OneFootball

Kaine Kesler-Hayden has struggled at Coventry City this season after his £3.5m summer move from Aston Villa

With 11 matches of the 2025-26 season remaining, Coventry City finally have one foot in the Premier League after two Championship play-off disappointments in the last three years.

The Sky Blues reached the final three years ago, losing to Luton Town on penalties after a 1-1 draw over 120 minutes, and it was a 3-2 defeat in the semi-finals to Sunderland last year that kept them from returning to Wembley once more.

Frank Lampard's side are now heavily odds-on to win promotion to the top flight of English football, sitting nine points ahead of third-placed Millwall in the standings, with only Middlesbrough between the two as it stands.

Cov have not competed in the Premier League since 2001, and are looking to end a 25-year wait to return.

There are sure to be many twists and turns between now and the final whistle of the 46th game of the campaign, and Coventry will need to be at their best for the final months of the term to keep their place inside the top two - not every player under Lampard though has thrived at the CBS Arena this season.

Kaine Kesler-Hayden’s Coventry City struggles have been unexpected

Kaine Kesler-Hayden arrived at Coventry City last summer with a lot of expectations after his impressive loan spell at Preston North End in the previous campaign.

The full-back made the switch to the Sky Blues from Aston Villa in a deal worth a reported £3.5 million after he received the Lilywhites’ Player of the Season award for his performances at Deepdale.

North End of course would've loved to have landed Kesler-Hayden on a permanent basis, but they were never realistically in the running due to their finances, which led to Coventry stealing a march on other Championship clubs.

His signing was seen as a real coup for Lampard’s side following his displays for the Lancashire outfit, but after several months of the season it’s clear that things aren’t quite working out as hoped.

Kesler-Hayden proved a versatile and exciting figure at Preston, but he now finds himself on the outside looking in at Coventry’s promotion push.

Such is the strength in depth of Lampard’s squad that the full-back is even missing out on being included in the matchday squads in recent weeks.

He made his return to the side for the first time since January 1 in their 2-1 win over Sheffield United last week, but he only came off the bench in the very final moments of the game.

He started against Charlton Athletic on New Year's Day, but has barely played a single minute in the weeks since, with Milan van Ewijk and Jay Dasilva locking down the two positions on the flanks in Coventry’s backline.

It's not entirely surprising that Van Ewijk is such a core component of the squad given he has contributed seven assists so far this season already, making him a crucial attacking threat.

Meanwhile, Dasilva may not have the same level of assists, he is still creating 1.25 chances per 90 (per Opta), and he provides a level of defensive solidity that is much-needed on the left flank.

Worryingly, if Kesler-Hayden’s not even making matchday squads in the Championship, he’s at risk of being frozen out completely if the club do earn promotion to the Premier League this campaign.

In that case, a summer move may even be on the cards and Coventry will have to recoup as much of the £3.5 million they paid to sign him in order to salvage something from this transfer.

Perhaps there was a thought that Van Ewijk may have been sold last summer by Coventry and Kesler-Hayden was the succession plan, but the Dutchman ended up staying and has even signed a new contract since, and with top flight football looking likely, remaining at the CBS Arena looks guaranteed for the number 27.

Preston North End will be shocked at Kaine Kesler-Hayden’s struggles

Kesler-Hayden was excellent for Preston last season, and manaher Paul Heckingbottom will be very disappointed seeing how much he’s struggled this year.

The Lilywhites were unable to compete with Coventry for his permanent signing from Aston Villa, and it’s not worked out for anybody that he’s at the CBS Arena.

While Heckingbottom’s side have improved overall compared to last year, albeit their play-off challenge is fading, it’s easy to think what Kesler-Hayden could be adding on top if he had instead stayed at Deepdale.

Perhaps if Coventry are promoted, and he continues to be out of favour under Lampard, a return to the club could be on the cards, if North End could find the funds.

Kesler-Hayden contributed two goals and three assists for the Lancashire outfit last season, which doesn't look outstanding on paper, but his attacking energy and drive was noticeable on the pitch, and someone of his ability would be more-than welcome at the club, if he could recapture that form.

But a return would ultimately be a disappointing outcome for the defender when it comes to his Coventry career, who will be walking away from a possible Premier League team in order to turn his career around.

Kesler-Hayden seemed to be heading for big things after being Preston’s star player last season, so to end up back at Deepdale could be a bit of a step backwards for his development.

The concern will be that he's not capable of taking the step up to an automatic promotion-chasing Championship side, and that competing for a relegation-threatened side is his level.

But there is still time left in this season for the full-back to turn things around and to get his time at Coventry back on track, but he will need to start putting in performances quickly, because Kesler-Hayden’s time with the Sky Blues is already at risk of never working out after only signing for the club last summer.