Every football club gets some transfers right and some transfers wrong. Coventry City’s first spell in the Premier League, from 1992 to 2001, had plenty of both. For every inspired deal – a Dion Dublin, a Gary McAllister, a Robbie Keane – there was a signing that never made sense, never settled, and never delivered.
Fast forward to 2026, and the Sky Blues are back among the big guns. Frank Lampard’s side powered to the 2025-26 Championship tile with 95 points, miles clear of the trailing lot.
The club have already added seven new arrivals ahead of their top-flight return. The challenge now is to avoid repeating the mistakes of their Premier League adventure which ended in 2001 after nine years of narrow escapes and, at times baffling recruitment.
FootballWhispers looks at the bottom end of the scale – the five worst signings from Coventry’s original Premier League years.
This list is not just about goals or clean sheets. It is about players who simply did not work out, whether because of poor form, a lack of games, or a move that never made sense in the first place.
5. Oleksandr Yevtushok
Signed in 1997 from Ukraine as an international defender for £1m (€1.20m), Oleksandr Yevtushok arrived with little fanfare and left with even less. He was the first Ukrainian to play in the Premier League.
Usually called Alex Evtushok by the English media, the 1.88m tall centre-back made just three Premier League appearances for Coventry. He spent most of his time on the bench or outside the matchday squad entirely.
The pace and physicality of English football often appeared to overwhelm him, and he never looked comfortable in a struggling defence.
For a club that needed reliable, ready-made performers on a tight budget, this was a recruitment punt that ultimately proved wasteful. Yevtushok eventually drifted away without any real impact, moving back to Ukraine on a free transfer and leaving Coventry with a transfer deficit.
4. Viorel Moldovan
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The Sky Blues made Viorel Moldovan one of their most expensive signings in 1997, paying Swiss side Grasshoppers 10 million Swiss francs i.e. around £2.82m (€3.30m). He was Coventry’s most expensive signing of the season.
Moldovan arrived with a reputation as a proven goalscorer, but the Premier League proved a very different challenge. The Romanian international managed only two league goals in 14 appearances, often looking isolated and short of sharpness.
He never looked like the penalty-box predator Coventry had paid for. In a side fighting relegation that lack of cutting edge proved costly. Moreover, Dion Dublin and Darren Huckerby were first choice under coach Gordon Strachan.
Within a year he was gone, moving on to Fenerbahce. Coventry, however, made a slight profit on his £3.59m (€4.20m) departure fee. But the transfer ultimately was a failed one.
3. Liam Daish
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Liam Daish arrived for around £1.3m (€2.30m), with Coventry hoping he would add steel to a leaky defence after impressive spells at Cambridge United and Birmingham City.
Instead, he quickly looked out of his depth in the Premier League, where his lack of pace was badly exposed. Daish made around 34 appearances over three years. He never once looked like the commanding centre-back Coventry needed.
He contributed virtually nothing and was part of a defence that continued to ship chances, leaving the club in familiar relegation trouble.
Daish was moved on quickly, transferring to non-league side Havant & Waterlooville for free. His signing came to represent money wasted.
2. Eoin Jess
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Hoping to add creativity and goals from midfield, Coventry City paid Aberdeen around £2.6m (€3m) in the 1996 winter transfer window for Eoin Jess.
The Scottish international made his name with Aberdeen for seven years before moving to England, racking him 201 appearances in his first spell. But he never came close to reproducing that form in the Premier League.
The then 25-year-old managed only a handful of goals during his short stay at Coventry, including a forgettable own goal against Manchester United, a poor return for a player signed to provide attacking spark.
Jess drifted through matches without influencing them. For every flash of skill, there were long spells where he simply disappeared. The Scot was sold back to Aberdeen a little over a year later for £900k (€1.1m) – less than half the price they paid for him.
1. Craig Bellamy
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Robbie Keane’s handsome transfer fee to Inter Milan permitted Coventry City to invest in another star forward. Craig Bellamy became Coventry’s record signing in August 2000 for £7.9m (€9.25m), quite reluctantly.
The Welsh attacker reportedly wanted to join Newcastle United instead, citing Coventry’s persuasive techniques as the reason he moved to the Midlands.
Bellamy was young, quick and highly rated, but he delivered only eight goals in a struggling side across 37 appearances. His arrival was meant to solve Coventry’s scoring problems, yet he never looked like the ruthless finisher they needed.
At the end of the season, Coventry were relegated to the second division. What made it worse was Bellamy’s public declaration: “I never once enjoyed it at Coventry. I felt quite demoralised. I had enjoyed myself so much at Norwich – but I found I had taken a backward step.”
Coventry, however, made vey little loss financially from his departure.