Ten top-flight superstars who suffered nightmare stints in lower-league dugouts

Going down the leagues to make your name as a manager isn't easy. And if you fail once, writes Richard Edwards, you’re lucky if you get another crack at it...

Jimmy Floyd Hasselbaink was an incongruous sight in the away dugout at Wycombe on Monday – and after guiding Burton Albion to a 3-1 win in his first match in charge, the Dutch goal-machine could be forgiven for thinking that this management lark is as easy as smashing a pig’s bladder in the back of an onion bag. FFT, though, has some words of warning for the former Chelsea goal-getter. Just check out the motley crew below...

Tony Adams, Wycombe, 2003

“I’ve been enjoying my sports science degree at university, which I’m halfway through, but it feels right to be here now,” said Tony Adams at his Wycombe unveiling in November 2003. Club director Alan Parry clearly felt the same.

“We had the same feelings when Martin O’Neill walked in here,” he said. The current Republic of Ireland boss walked out of Adams Park a hero, having successfully navigated the club into the Football League. Adams took them in the opposite direction, overseeing relegation from League One.

That said, he was hardly given a huge budget to turn around this sinking ship. “One day I lost a player because the chairman refused to pay the £90 he wanted for a TV licence,” he would later tell The Daily Mail. Spells at Portsmouth and Gabala followed. Success didn’t.

"Alright everybody. Don't worry, I'm not stopping long."

Bobby Moore, Southend United, 1984

Moore's limited spell in management and coaching remains an irremovable stain on his career. And if the World Cup-winning captain thought a stint at Roots Hall in the mid-80s would boost his chances of getting a job elsewhere he was left sorely disappointed. First appointed as manager in February 1984 – just months after being named the club’s chief executive – he steadied the ship but left his role just two years later with the Shrimpers anchored in Fourth Division obscurity. “I don’t know what the future holds,” he said on his departure. It was his last managerial job.

Peter Shilton, Plymouth, 1992

Shilton was still playing when he left Derby and headed south to join Plymouth as player-manager. “I see the job as a tremendous challenge,” he said in March 1992. He couldn’t have been more right. The Pilgrims were relegated from the Second Division just two months later, Shilton’s reign little short of disastrous. His rapport with chairman Dan McCauley made the relationship between Russia and Ukraine look positively cordial, while his players, bizarrely, were threatened with a fine if they offered an opinion of their own in interviews. In fairness, his Plymouth side scored goals aplenty but when gates dipped to a nine-year low, Shilton was off – and never to return to management again.

Shilts and his fetching tracksuit didn't last long

Bobby Charlton, Preston

“I have always admired Preston and I think the club has tremendous possibilities,” said Charlton in May 1973. But after the Lilywhites were relegated from the Second Division in his first season in charge, the England legend was on a hiding to nothing. He even decided to don the boots again to demonstrate the art of goalscoring to his hapless side, scoring his 200th league goal against Walsall in September 1974 – a strike which proved a rare highlight in an otherwise unforgettable reign. He resigned in the summer of 1975 over the sale of club captain John Bird to Newcastle. “It has been a matter of principle,” he said. He was never tempted into returning.   

Tommy Lawton, Brentford

As a goalscorer, the princely Lawton towered above his peers. When it came to decision making? Not so much. Lawton’s decision to leave Chelsea for Third Division Notts County in 1947 remains one of the most baffling in history, and his first foray into management caused equal amounts of head scratching. A number of high-profile sides were rumoured to be queuing up to offer him a return to the top flight, but when he did move, in 1952, it wasn’t to Old Trafford or Highbury but to Brentford’s Griffin Park. “There was no smooth transition to management,” wrote Ivan Ponting in The Independent’s Lawton obituary in November 1996. “He was booed for the first time in his life, to which he took grave exception, and before long he resigned.”

Lawton later decided a life behind the bar was easier

Kerry Dixon, Doncaster

Former boss Sammy Chung didn’t even know Dixon had been appointed until he opened the door to his former office and found the former Chelsea and England man sat behind his desk just 90 minutes before the opening game of the 1996/97 season. Dixon remained in charged for a full season at the club’s then-home, Belle Vue, but left after three games of the following campaign. An 8-0 League Cup humping by Nottingham Forest proved to be the final straw. He went down fighting, though, insisting the team for that game wasn’t picked by him but by chairman Ken Richardson.

Ian Rush, Chester City

Former team-mate Mark Lawrenson expressed doubts about Rush’s ability to cut it in management before the ink was dry on his contract at Chester City – although the Welshman gave his ex-colleague, and presumably former friend, short shrift. “What he said was an insult not only to me, but to those running Chester who I know interviewed many outstanding candidates before they appointed me.” As it is, Lawro’s punditry career comfortably outlasted Rush’s in management, although in mitigation Chester were already well on the road to disaster when he took over in August 2004. It remains his sole spell in management. Once bitten, twice shy.

Not even his old team-mates thought Rush could cut it at Chester

Stanley Matthews, Port Vale

As a flying winger, Matthews, the Wizard of Dribble, was quite simply magic. And when he called time on his astonishing career at the age of 50 – think (roughly) Alan Pardew running out at St James’ Park in a figure-hugging Wonga-emblazoned shirt rather than a suit – he decided, quite naturally, that a career in management beckoned. As it was, his three-year stint at Port Vale was a complete shocker. The club was fined for financial irregularities and was turfed out of the league. All without Matthews ever claiming a penny in wages. He too would never set foot in the dugout again.

Chris Sutton, Lincoln City

Once English football’s most expensive player when he signed for Blackburn from Norwich for £5m (or half a Ross McCormack in modern parlance), Sutton was also labelled one of English football's most difficult characters, making him perfect managerial material. FFT can confirm that this persona was more fiction than fact, but he had little to smile about at Sincil Bank. He resigned in September 2010, a year after taking the job, citing ‘personal reasons’. He hasn't taken the reins anywhere else.

Sutton called time on his stint at Sincil Bank for family reasons

Edgar Davids, Barnet


"No.3 was uncomfortable for him and I had given the rest out," said Arsene Wenger. "I thought it might be a good idea to give the No.10 to a defender."

Matt Allen on football's wackiest shirt numbers

No one saw the appointment of the former Netherlands international coming, and even fewer thought he would hang around when the club were relegated to the Conference under his watch. After relegation he took the No.1 shirt, claiming he would "start a trend" by doing so. Nevertheless, nobody could accuse Davids of taking an easy route into management and even fewer could claim he didn’t have the club’s best interests at heart. He played 36 league matches for the Bees and resigned in January with the club just three points off a play-off place. Whether he gets, or wants, another shot at management remains to be seen.