The last Coventry team to play Premier League football, then and now: “I had agreed a deal with Inter… and I still haven’t gotten over it”

The landscape of Premier League football has shifted drastically over the past two decades.

Just cast your mind back to the start of the century: Leeds United were still making noise in the Premier League table’s upper reaches, Manchester City had just suffered relegation, and Coventry were regulars in the top-flight.

In 2000/01 both Sky Blue clubs suffered relegation to what was then known as Division One (Leeds would join them a few years later, of course). There they stayed until 2012, when they dropped down another rung into English football’s third tier.

Only now, nine years on, have climbed back up. But the Midlands-based Sky Blues will now be hoping to follow in the footsteps of Sheffield United, Bournemouth and Southampton in more recent seasons, and use automatic League One promotion – awarded after clubs voted to curtail the season – as a catalyst to ensure their stay in the Championship is only fleeting.

The last time Coventry were part of the top tier was, in fact, 20 years ago under a certain Gordon Strachan. In his first managerial position, the former Manchester United midfielder led Coventry to consecutive mid-to-low table finishes.

In 2000/01, he was unable to prevent the ship sinking and the Sky Blues exited the Premier League, but that season gave several names you’ll probably be familiar with a platform from which they went on to succeed. Starting with…

Goalkeeper: Chris Kirkland

• Age: 39
• Appearances for Coventry: 29

It’s safe to say Chris Kirkland has had quite the career. From becoming the most expensive goalkeeper in British transfer history at the age of just 20, to having a Leeds supporter run onto the pitch and assault him, the one-capped England international has experienced the highs and the lows of the game.

But his first foray into the crazy sport came at Coventry during his formative years. When injury struck the club’s titanic No. 1 Magnus Hedman, Strachan needed a man to step into the equation and fill the Swede’s towering boots. Cue a fresh-faced Kirkland.

Given his frame, though, Strachan could hardly avoid him. As legendary Coventry ‘keeper Steve Ogrizovic once explained: “Chris was on his paper round and had to be called in as a late replacement. Even then he stood out. Partly it was his size. Even at 15 he must have been 6 ft 4 ins.”

His baptism of fire was a 2-1 win over Tottenham but his second match saw him receive a straight red card in the 22nd minute as his side lost 6-1 to Chelsea. That defeat, coupled with Strachan describing him as a “big Bambi who couldn’t kick the ball out of the penalty box”, would have been enough to make any man crumble.

But Kirkland kept his nerve and went on to clinch the club’s Players’ Player of the Year award that season before making a £6m move to Liverpool. He never quite held down a consistent berth at Anfield, though he was Rafa Benitez’s main man for the Group Stages in Liverpool’s 2004/05 Champions League triumph.

Kirkland went on to star for Wigan but also enjoyed spells at Leicester, Doncaster, Sheffield Wednesday, Preston and Bury before calling time on his career and moving into coaching, first with Port Vale, Liverpool Women and now Colne.

Right-back: Paul Telfer

• Age: 46
• Appearances for Coventry: 149

The Edinburgh-born defender began his career as a right-sided midfielder for Luton in 1988 and went on to make over 100 appearances for the club before moving to Coventry in 1995.

The one-time Scotland international is the nephew of former Chelsea midfielder Eamonn Bannon and went on to reach the FA Cup final with Southampton in 2003, as well as winning back-to-back Scottish Premier League titles with Celtic.

Centre-back: Gary Breen

• Age: 46
• Appearances for Coventry: 149

West Ham fans will be having none of it, but during his time at Coventry, Breen was once being courted by European royalty in Inter Milan and Barcelona. The London-born Irishman was a near ever-present in 2000/01 but was unable to help the club retain their Premier League status, and despite plying his trade in the second tier the following campaign, Mick McCarthy named him is his squad for the 2002 World Cup for Republic of Ireland.

The infamous Roy Keane incident, in which the Man Utd midfielder was sent home after a quarrel with McCarthy, remains a painful footnote in the nation’s World Cup campaign that year, but the Green Army will never forget their unbeaten Group Stage run and nearly knocking out Spain.

Integral to that run was Breen, who played in the 3-0 win over Saudi Arabia (in which he scored) as well as draws with Germany and Cameroon. However, their hopes were dashed by Spain in the Round of 16 where they lost on penalties. To take that side, including Raul, Iker Casillas and Carles Puyol, to a sudden death shootout was, and still is, a commendable feat.

Following his imperious showings in South Korea and Japan, Breen was said to be on the wishlist of both Inter and Barca, but a move, unfortunately, did not transpire after he failed a medical at the former, which he still rues to this day.

“Prior to the Spain game, I had agreed a deal with Inter,” Breen said.

“When we got back to Dublin, I flew out to Milan. I had the medical, failed the medical, and I still haven’t gotten over it.”

Centre-back: Richard Shaw

• Age: 51
• Appearances for Coventry: 322

This Coventry hall-of-famer was also part of Crystal Palace’s helter-skelter existence in the 90s, suffering relegation and gaining promotion almost on a season-to-season basis. But in 1995, he decided to cut his teeth further north and joined the Sky Blues.

Shaw went on to play for them for over a decade, clinching the club’s Player of the Year accolade on two occasions (1998/99 and 2001/02) and earning a testimonial against Celtic in 2006. Over 25,000 fans packed the Ricoh Arena to watch the legend in action as Coventry ran out 3-1 winners.

Shaw has since moved into coaching, taking positions at Millwall, Coventry and more recently Crystal Palace, though he left his role as U23 coach last year.

Left-back: Marc Edworthy

• Age: 47
• Appearances for Coventry: 78

In the 90s, Crystal Palace were the very definition of a yo-yo club and having once again suffered the drop in 1997/98, Coventry couriered £1m over to Selhurst Park to secure the services of Edworthy. The versatile defender spent four years at Highfield Road but never managed to recapture the form he showcased with the Eagles and suffered his second career relegation in 2001. Edworthy remained at Coventry for one more year, but made the short journey to Wolves in 2002, before leading a nomadic existence in English football, representing Norwich, Derby, Leicester and finishing up at Burton in 2009.

Central midfield: Lee Carsley

• Age: 46
• Appearances for Coventry: 52

The Birmingham-born scrapper is best remembered for his Everton days, where he went on to forge a important part of David Moyes’ central midfield. But before Goodison Park, the former Republic of Ireland international was showcasing his terrier-like exploits at Coventry, albeit very briefly.

Carsley joined Strachan’s side midway through the 2000/01 campaign and immediately cemented a place in the Scot’s starting XI. He added bite and a new aggression to the centre of the park but was unable to prevent the club’s relegation. He left Coventry in March the following season, despite high hopes the club would succeed in making an immediate return to the top flight.

Central midfield: John Eustace

• Age: 40
• Appearances for Coventry: 98

The former Watford skipper was just learning the ropes when he was trying to keep Coventry afloat in 2000/01. Despite his best efforts, the Sky Blues ultimately dropped down to the Championship, though Eustace’s showings were enough to see him named captain the following season despite his young age. What promised to be a hard-fought 2001/02 campaign, in which Coventry would attempt to bounce back immediately, Eustace suffered a knee injury in September which ruled him out for seven months.

Right midfield: David Thompson

• Age: 42
• Appearances for Coventry: 72

The Birkenhead-born midfielder began his career at Liverpool and looked to be making progress in the first team after winning the 1996 FA Youth Cup, in a side that included Jamie Carragher and Michael Owen. Despite featuring 31 times in the 1999/2000 season, Thompson became disillusioned with his prospects at Anfield and ultimately left for Coventry.

The diminutive midfielder was a hit in the Midlands and joined the Sky Blues with pedigree, but even his best efforts weren’t enough to save Coventry. He shone the following campaign in the old First Division, scooped the club’s Player of the Year award, and joined Blackburn under Graeme Souness. Despite the slight resurgence, Thompson still speaks of his Liverpool days with a tinge of sadness.

“I regret leaving Liverpool,” Thompson told the Athletic. “It’s the best club in the world with the best people and the most qualified people. The football was at the highest level. I felt like I was on a similar wavelength with the players around me.

“At Coventry, it wasn’t the same. We had players who were triers but they weren’t at the same standard. We’d have the ball 30 per cent of the time whereas at Liverpool, it’d be 70. This created a problem for me because I felt as though I had to work miracles when I did get it.”

In 2003 he was called up for England by Sven-Goran Eriksson, but a knee injury kept him sidelined for several months. Thompson never recovered fully from this and was forced to retire at 29.

Left midfield: Craig Bellamy

• Age: 40
• Appearances for Coventry: 39

With Robbie Keane moving to Inter Milan in the summer of 2000, Coventry desperately needed a replacement forward. Bellamy was flourishing for Norwich City during his early years in football and prompted Strachan to fork out a club-record £6m for his services.

Bellamy never actually wanted to join Coventry City. He instead wanted to go to Newcastle United, but they were stalling on an formal offer and so Strachan stole a march to set up a face-to-face meeting.

Bellamy didn’t have an agent at the time. What he did have was an inexperienced financial adviser who, unbeknown to his client, had sought out the advice of John Fashanu. In turn, Fashanu “invited himself along […] to ensure [Bellamy] didn’t get taken for a ride.”

Bellamy had never actually met the former Wimbledon player, whose sudden appearance was so confusing that he was virtually embarrassed into a verbal agreement with Coventry.

In his Autobiography, ‘Goodfella’, Bellamy recalled: “They were persuasive. I felt undermined by the mess with Fashanu. I wanted to save face with Strachan. I felt stressed. My chest was tight because I’m asthmatic. I was struggling to breathe properly because I was so tense. I was in a state. So I did what everybody had told me not to do. I told Strachan I’d sign.”

Hours after signing a contract with Coventry, Bellamy received a text from then-Newcastle manager Sir Bobby Robson, which read: “Hello son. Good news. Our bid’s in.”

The Welshman was a near ever-present in the relegation season, finishing the campaign as Coventry’s joint-highest scorer. He would ultimately leave for Newcastle the next summer and has gone on to play for an elite band of clubs, including Liverpool, Man City, West Ham, Celtic, Blackburn and Cardiff. He is now an U21 coach for Anderlecht.

Despite playing for Coventry for just one season, Bellamy had few positive memories of his experience: “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.”

Attacking midfield: Mustapha Hadji

• Age: 48
• Appearances for Coventry: 62

Hadji first rose to major prominence after scoring spectacular goals for Morocco at both the 1998 Africa Cup of Nations and World Cup before beating Jay-Jay Okocha to the African Footballer of the Year award. All of which encouraged Coventry to splash out on a then club-record £4m deal on the attacking midfielder from Deportivo La Coruna during the following summer.

The move apparently prompted a boom in the Midlands fez industry, with a number of those flat-topped crimson hats turning up at Highfield Road in homage to their latest star.

Indeed Hadji proved a hit at Coventry. His crowning moment came when he bagged a first-half brace against Aston Villa in the penultimate game of the season. Coventry needed three points to have any hope of staying up, but their rivals battled back and won 3-2, and were so impressed by the performance of Hadji that they signed him that same summer.

He won the Intertoto Cup with Villa in 2001, and went on to play for Espanyol, Emirates Club, Saarbrucken and Fola Esch. He is now assistant manager for the Morocco national side.

Striker: John Hartson

• Age: 45
• Appearances for Coventry: 12

Having burst onto the scene for Luton, the Welshman became the most expensive British teenager when Arsenal spent £2.5m on his signature in 1995. During his time in north London, Hartson faced fierce competition up-top, but the acquisition of Dennis Bergkamp to partner Ian Wright in the final third signalled the end of his time at Highbury and he joined West Ham.

After a fruitful spell for the Hammers and Wimbledon, Hartson joined Coventry midway through the 2000/01 season. He shone the moment he walked onto the pitch, scoring six goals in 12 games and finishing the joint highest-scorer despite playing just half the season. Had Hartson – and Carsley – been at the club in the summer, their chances of survival would have been favourable.

Coventry were naturally reticent to allow Hartson to leave, but £6m persuaded them to accept an offer from Celtic.

Honourable mentions: Youssef Chippo, Ysrael Zuniga, Carlton Palmer, Jay Bothroyd