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Struck down in their prime by injury, starved of first team football by a manager that just didn’t see the potential, or just a player in the wrong place at the wrong time – Wanderers’ history is littered with cases of ‘what might have been’.
Though some footballers only have themselves to blame when things do not work out at a club, sometimes you have to accept that fate has dealt them a bad hand.
Here we look at those who could have been great, the nearly men who but for one stroke of misfortune or with a different man in charge could have been heroes.
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14. Sean Davis
It had been the intention of Gary Megson to build his side around the creative talents of former Portsmouth man Davis, who was in the peak of his career at 29 years old.
Wanderers had tried to sign him 12 months earlier and were turned down with a £3.5million bid. This time, they got him on a Bosman.
His Bolton career would last just three-and-a-half competitive games, however, as following a red card against Liverpool he picked up a serious knee injury which kept him out competitive football for the next 30 months.
A brief loan spell at Bristol City proved to be the last hurrah for Davis, who always maintained his knee injury had not been managed well during his rehab.
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13. Max Clayton
The promising young striker came to Wanderers from Crewe in a rather convoluted fashion - and had been staying in Denmark ahead of a possible move when Dougie Freedman finally convinced Bolton to make their move.
The youngster had been chased by some top clubs and trialled at Wolves and Sunderland and commanded a £300,000 fee at tribunal. But by the time he debuted for Wanderers in a 2-1 home defeat to Bournemouth he had not played in nearly a year because of a broken ankle.
After nine appearances he appeared to be making progress but then got struck down by a knee injury against Ipswich which kept him out for another six months.
He returned in September 2015 to play in a 2-2 draw with Brighton but the comeback would last just two months - a freak hamstring tear sidelining him for another year.
Clayton did return in the promotion season of 2016/17 to play 13 times, scoring a memorable late equaliser at Coventry but his potential was never fully realised before leaving for Blackpool the following summer.
12. Neil Redfearn
One of a cluster of homegrown players who came through the ranks at Burnden Park in the early eighties, Redfearn was in the same alumni as Warren Joyce, Wayne Foster, Simon Farnworth and Steve Thompson. Wanderers' financial issues forced them to grab at a £40,000 offer from Lincoln City in 1984 - a decision which looked plain daft as he carved out a solid Football League career and played for the likes of Barnsley, Bradford and Charlton in the top flight.
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11. Benik Afobe
Young and relatively unknown when Owen Coyle brought him to Bolton on loan from Arsenal, Afobe scored a pre-season hat-trick at Tranmere but struggled to make a dent in a team which looked ill-at-ease in the Championship. A change of manager failed to help as Dougie Freedman told him almost instantly that his services would no longer be required - and Bolton signed Craig Davies instead.
10. Dean Holden
Just before the turn of the millennium, Holden - a former England youth international - was being tipped to be the Bolton right-back for the next decade.
Sam Allardyce rated the Salfordian highly but a broken leg sustained after coming on a sub at Sheffield United in March 2000 took a year to recover from, by which time the club had moved on.
Holden's loss was Nicky Hunt's gain - and though he went on to have a solid career, you can't help but wonder what might have been for the current Bristol City assistant boss.
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9. Tom Eaves
As a teenager, the lofty striker had impressed sufficiently with a hat-trick for Oldham against Bolton in a pre-season friendly to convince the club to commit to a deal worth £1million. Eaves was billed as a younger version of Kevin Davies but he spent six long years waiting for a chance to prove it.
Injuries were an issue - but an eternity spent out on loan and in the nether regions of the development squad did nothing for his development.
Eaves had the last laugh. After rejuvenating his career at Gillingham he earned a move to Hull City and has 48 goals in the last three seasons.
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8. Derik Osede
Plucked by Neil Lennon from Real Madrid's feeder club Castilla, Derik had pedigree and a languid style which stood him apart from anyone else in the Bolton squad.
Sadly, Lennon nor his successor Phil Parkinson could find a position that suited him. And despite clear natural footballing talent the Spanish defender-midfielder spent too long on the fringes before leaving the club.
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7. Fabrice Muamba
The story of Muamba's collapse at White Hart Lane and his miraculous recovery has been told many times - and it is a blessing to think he is around to read himself in this list today.
But the really selfish point in the former midfielder's incredible tale is that had he been available in the closing months of the campaign, his combative qualities might just have given Owen Coyle's side enough to avoid relegation from the Premier League.
6. Arnar Gunnlaugsson
Wanderers love to rave about their foreign legion - but the tale of Icelander Gunnlaugsson rarely gets a mention. Top scorer with 14 goals when he fell out with Colin Todd midway through the 1998/99 season, he was effectively replaced by Bo Hansen. But those goals sure would have come in handy in a season that finished with Wembley disappointment against Watford.
5. Neil McNab
A ball of midfield energy who cost £250,000 from Tottenham - where he had been the club's youngest-ever player - injuries meant McNab didn't feature as much as he would have hoped in Wanderers' return to the top flight.
He seized the number 11 shirt the following season but after Ian Greaves was sacked at the turn of 1980, Stan Anderson cashed in on a £220,000 offer from Brighton to help him rebuild an ageing side.
McNab went on to achieve huge success at Manchester City, showing Bolton what they have given up.
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4. Florent Laville
Played just 15 games for Bolton and yet got voted into the club's all-time 50 top players in 2005.
The Frenchman was loaned from Lyon in January 2003 and wasn't just good, he was brilliant. It was no surprise that Sam Allardyce brought him back the following season on a permanent deal - but just five games in he ruptured his cruciate ligament and never played for Wanderers again.
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3. Blerim Dzemaili
Swiss midfielder signed as a parting gift by Allardyce in 2007 - but who picked up a knee injury in his final weeks with FC Zurich which meant he missed the start of the 2007/08 campaign, By the time he was fit enough to play, Sammy Lee had exited the building and Gary Megson was not a fan. Playing just once as a substitute - against Sheffield United in the FA Cup - he was loaned out to Torino and eventually signed for the Serie B side for £1.2million. A fair profit, you might say, until you consider the multi-million pound moves he then made to Parma, Napoli and Galatasaray and the 69 caps he won for his country. What a waste.
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2. Stu Holden
There was no telling how good American Stu Holden was going to be - but by March 2011 most top clubs in the country were watching his every move and Bolton knew they had a very valuable asset on their hands.
Possessing the skills, the energy and the charisma, Holden had overcome some injury hurdles to become one of the Premier League's pound-for-pound best midfielders. And then with one reckless challenge, it was effectively over.
Manchester United's Jonny Evans saw red for the tackle that left Holden with a fractured knee and femur, plus 26 stitches, but he will never be forgiven by Bolton fans, nor Holden himself.
Efforts to come back were valiant but the subsequent breakdowns for club and country were heartbreaking.
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1. Mark Davies
'Sparky' had been compared to Paul Gascoigne in his teenage years at Wolves by ex-England boss Glenn Hoddle and there have been few players who have worn a Bolton shirt in the last two decades as aesthetically pleasing on the ball.
It is almost criminal to think, though, that in nine seasons, spread across three divisions, he played just 200 games.
Major injuries - to both his knees - curtailed a football career that would have surely ended up with international caps had Bolton, and Davies, managed to hang around in the Premier League.
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Struck down in their prime by injury, starved of first team football by a manager that just didn’t see the potential, or just a player in the wrong place at the wrong time – Wanderers’ history is littered with cases of ‘what might have been’.
Though some footballers only have themselves to blame when things do not work out at a club, sometimes you have to accept that fate has dealt them a bad hand.
Here we look at those who could have been great, the nearly men who but for one stroke of misfortune or with a different man in charge could have been heroes.
[You must be registered and logged in to see this image.]
14. Sean Davis
It had been the intention of Gary Megson to build his side around the creative talents of former Portsmouth man Davis, who was in the peak of his career at 29 years old.
Wanderers had tried to sign him 12 months earlier and were turned down with a £3.5million bid. This time, they got him on a Bosman.
His Bolton career would last just three-and-a-half competitive games, however, as following a red card against Liverpool he picked up a serious knee injury which kept him out competitive football for the next 30 months.
A brief loan spell at Bristol City proved to be the last hurrah for Davis, who always maintained his knee injury had not been managed well during his rehab.
[You must be registered and logged in to see this image.]
13. Max Clayton
The promising young striker came to Wanderers from Crewe in a rather convoluted fashion - and had been staying in Denmark ahead of a possible move when Dougie Freedman finally convinced Bolton to make their move.
The youngster had been chased by some top clubs and trialled at Wolves and Sunderland and commanded a £300,000 fee at tribunal. But by the time he debuted for Wanderers in a 2-1 home defeat to Bournemouth he had not played in nearly a year because of a broken ankle.
After nine appearances he appeared to be making progress but then got struck down by a knee injury against Ipswich which kept him out for another six months.
He returned in September 2015 to play in a 2-2 draw with Brighton but the comeback would last just two months - a freak hamstring tear sidelining him for another year.
Clayton did return in the promotion season of 2016/17 to play 13 times, scoring a memorable late equaliser at Coventry but his potential was never fully realised before leaving for Blackpool the following summer.
12. Neil Redfearn
One of a cluster of homegrown players who came through the ranks at Burnden Park in the early eighties, Redfearn was in the same alumni as Warren Joyce, Wayne Foster, Simon Farnworth and Steve Thompson. Wanderers' financial issues forced them to grab at a £40,000 offer from Lincoln City in 1984 - a decision which looked plain daft as he carved out a solid Football League career and played for the likes of Barnsley, Bradford and Charlton in the top flight.
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11. Benik Afobe
Young and relatively unknown when Owen Coyle brought him to Bolton on loan from Arsenal, Afobe scored a pre-season hat-trick at Tranmere but struggled to make a dent in a team which looked ill-at-ease in the Championship. A change of manager failed to help as Dougie Freedman told him almost instantly that his services would no longer be required - and Bolton signed Craig Davies instead.
10. Dean Holden
Just before the turn of the millennium, Holden - a former England youth international - was being tipped to be the Bolton right-back for the next decade.
Sam Allardyce rated the Salfordian highly but a broken leg sustained after coming on a sub at Sheffield United in March 2000 took a year to recover from, by which time the club had moved on.
Holden's loss was Nicky Hunt's gain - and though he went on to have a solid career, you can't help but wonder what might have been for the current Bristol City assistant boss.
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9. Tom Eaves
As a teenager, the lofty striker had impressed sufficiently with a hat-trick for Oldham against Bolton in a pre-season friendly to convince the club to commit to a deal worth £1million. Eaves was billed as a younger version of Kevin Davies but he spent six long years waiting for a chance to prove it.
Injuries were an issue - but an eternity spent out on loan and in the nether regions of the development squad did nothing for his development.
Eaves had the last laugh. After rejuvenating his career at Gillingham he earned a move to Hull City and has 48 goals in the last three seasons.
[You must be registered and logged in to see this image.]
8. Derik Osede
Plucked by Neil Lennon from Real Madrid's feeder club Castilla, Derik had pedigree and a languid style which stood him apart from anyone else in the Bolton squad.
Sadly, Lennon nor his successor Phil Parkinson could find a position that suited him. And despite clear natural footballing talent the Spanish defender-midfielder spent too long on the fringes before leaving the club.
[You must be registered and logged in to see this image.]
7. Fabrice Muamba
The story of Muamba's collapse at White Hart Lane and his miraculous recovery has been told many times - and it is a blessing to think he is around to read himself in this list today.
But the really selfish point in the former midfielder's incredible tale is that had he been available in the closing months of the campaign, his combative qualities might just have given Owen Coyle's side enough to avoid relegation from the Premier League.
6. Arnar Gunnlaugsson
Wanderers love to rave about their foreign legion - but the tale of Icelander Gunnlaugsson rarely gets a mention. Top scorer with 14 goals when he fell out with Colin Todd midway through the 1998/99 season, he was effectively replaced by Bo Hansen. But those goals sure would have come in handy in a season that finished with Wembley disappointment against Watford.
5. Neil McNab
A ball of midfield energy who cost £250,000 from Tottenham - where he had been the club's youngest-ever player - injuries meant McNab didn't feature as much as he would have hoped in Wanderers' return to the top flight.
He seized the number 11 shirt the following season but after Ian Greaves was sacked at the turn of 1980, Stan Anderson cashed in on a £220,000 offer from Brighton to help him rebuild an ageing side.
McNab went on to achieve huge success at Manchester City, showing Bolton what they have given up.
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4. Florent Laville
Played just 15 games for Bolton and yet got voted into the club's all-time 50 top players in 2005.
The Frenchman was loaned from Lyon in January 2003 and wasn't just good, he was brilliant. It was no surprise that Sam Allardyce brought him back the following season on a permanent deal - but just five games in he ruptured his cruciate ligament and never played for Wanderers again.
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3. Blerim Dzemaili
Swiss midfielder signed as a parting gift by Allardyce in 2007 - but who picked up a knee injury in his final weeks with FC Zurich which meant he missed the start of the 2007/08 campaign, By the time he was fit enough to play, Sammy Lee had exited the building and Gary Megson was not a fan. Playing just once as a substitute - against Sheffield United in the FA Cup - he was loaned out to Torino and eventually signed for the Serie B side for £1.2million. A fair profit, you might say, until you consider the multi-million pound moves he then made to Parma, Napoli and Galatasaray and the 69 caps he won for his country. What a waste.
[You must be registered and logged in to see this image.]
2. Stu Holden
There was no telling how good American Stu Holden was going to be - but by March 2011 most top clubs in the country were watching his every move and Bolton knew they had a very valuable asset on their hands.
Possessing the skills, the energy and the charisma, Holden had overcome some injury hurdles to become one of the Premier League's pound-for-pound best midfielders. And then with one reckless challenge, it was effectively over.
Manchester United's Jonny Evans saw red for the tackle that left Holden with a fractured knee and femur, plus 26 stitches, but he will never be forgiven by Bolton fans, nor Holden himself.
Efforts to come back were valiant but the subsequent breakdowns for club and country were heartbreaking.
[You must be registered and logged in to see this image.]
1. Mark Davies
'Sparky' had been compared to Paul Gascoigne in his teenage years at Wolves by ex-England boss Glenn Hoddle and there have been few players who have worn a Bolton shirt in the last two decades as aesthetically pleasing on the ball.
It is almost criminal to think, though, that in nine seasons, spread across three divisions, he played just 200 games.
Major injuries - to both his knees - curtailed a football career that would have surely ended up with international caps had Bolton, and Davies, managed to hang around in the Premier League.
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