Fans of a certain age are still hurting over the memory of selling a certain beloved Danish goalscoring midfielder to rivals Blackburn Rovers, younger fans will look to the sale of a recent England captain for a measly few million, and this season alone we've seen our two most promising youngsters for a combined fee that equates to one third of Robbie Brady.
So with that in mind, here is our blow-by-blow timeline of Wanderers’ persistent failings in the transfer market.
23rd September 1999, Per Frandsen to Blackburn Rovers: £1.75m
For anyone who's not old enough to remember the Danish midfielder, Frandsen was amazing. His sale to Blackburn was enough to force manager Colin Todd to resign, that's how good he was. My personal favourite memory was Frandsen scoring a screamer to open the scoring in the vital final game of the season victory over Middlesbrough at the Reebok to keep us in the Premier League.
We then bought Frandsen back from Blackburn a year later for £150,000 less than we sold him for. So I guess it's good that we made some money from the debacle eventually. Frandsen amassed 304 appearances and 39 goals for Bolton in his two spells at the club. He then finished his career with Wigan, obviously.
20th June 2000, Eidur Gudjohnsen to Chelsea: £5m
Eidur racked up 26 goals in 73 games for Wanderers, but failure to reach the Premier League - as a result of the farcical Play-Off semi final against Ipswich Town - meant a sale was likely. In came Chelsea, and for just £5m they plucked our best player away from us.
Eidur went on to create one of the Premier League's most feared striking partnerships in tandem with Jimmy Floyd Hasselbaink at Stamford Bridge. He hit double figures in four of his six seasons with The Blues before moving to Barcelona, making 112 appearances for the Catalans, winning the Champions League and La Liga. But he was only worth £5m apparently.
20th July 2000, Claus Jensen to Charlton: £4m
Just one month after the sale of Eidur, the lack of promotion led to the sale of another gifted Danish midfielder. Jensen made 113 appearances for Bolton before being sold on to Charlton Athletic for a paltry £4m. He went on to make 123 appearances for the south London side and earned 47 caps for Denmark.
8th November 2000, Mark Fish to Charlton: £700,000
2000 really was the year of the sale at Wanderers. Three years after signing from Lazio for £2m, fans' favourite Mark Fish was also farmed out to Charlton for nearly a third of that figure. Feeeeesh went on to make over 100 appearances for the Addicks, and made us look like right mugs for selling him so cheaply.
3rd February 2004, Jonathan Walters to Hull: £50,000
This is a bit of a strange one, as I don't remember Walters having that much promise as a youngster at Bolton. But he has to be included on this list when you look at what he's gone on to achieve in the Premier League with Stoke City, and that FA Cup semi-final at Wembley is really galling.
Walters made only four Premier League appearances at Bolton and scraped around the lower leagues for several years with the likes of Wrexham and Chester City. But he earned a big move to Ipswich Town then moved on to Stoke for £2.75m in 2010 and has made 219 appearances for The Potters and won 46 caps for Republic of Ireland. A case of what could have been, you could say.
16th January 2012, Gary Cahill to Chelsea: £7m
Cahill had become not only our best defender, but our only good defender and his departure left us all but doomed to relegation. The fact that we only got £7m for an international defender in the prime of his career was made even more galling by the club choosing to spend nearly half of that money on Marvin Sordell. Great business.
Has he done anything since, I hear you ask. Well... the season that he left us he went on to win both the Champions League and the FA Cup with Chelsea, he’s since won the Premier League and is on the verge of winning it again, and he’s won the Europa League and the League Cup. He’s also been named in the PFA Team of the Season twice and he’s captained England. And we only got £7m for him.
22nd July 2016, Rob Holding to Arsenal: £2.5m
Holding’s big move to Arsenal last summer again saw us sell our best defender for a transfer fee that was equally, if not even more, galling for Wanderers fans.
Holding had only made his debut for Bolton at the start of last season, but he made an instant impression and put in a series of outstanding performances en route to becoming our Player of the Season. Frankly, he was the only bright spark in a dreadful season as we were relegated to the third tier of English football for the first time in 23 years.
Bolton somehow managed to get only £2.5m for a player that had already impressed at England Under-21 level. This in the same summer as John Stones moved to Manchester City for £50m - that’s 20 times more than we got for Holding.
True there are probably add-on fees that haven’t been revealed, but it’s such a small fee for what was our best player - in a deal which saw Bolton sell their player of the season for the second summer in a row, after Tim Ream moved to Fulham 12 months previously.
Holding has already put in a few promising performances for Arsenal, and played in the Champions League. Yet he cost just £2.5m in this mad world of crazy transfer fees.
31st January 2017, Zach Clough to Nottingham Forest: £3m
Yet again the sale of Zach Clough saw Bolton sell their best player for peanuts. Clough was our top goalscorer not only this season, but the player at the club who had scored most goals for the club full-stop. Without him our promotion push now seems less likely, and if he had got us promoted then we could have got more money for him next summer.
However, rumour has it that the club simply had to sell Clough to keep afloat, but the fee of £3m to a club in the lower reaches of the Championship seems far too low. Clough has already made his debut for Forest and you suspect he will be an excellent signing for them this season. However, the transfer fee is made more galling by the fact that Forest sold their own youth talent Oliver Burke for £13m - more than four times what they paid for Clough - in the summer.
A couple of decent deals...
Away from the disappointment, there surely have to be some decent deals done. Right? Well, I'm struggling here but, here's a few where we have potentially done alright:
30th January 2009, Kevin Nolan to Newcastle: £4m
Youth academy product, team captain and proven goalscorer Nolan may have been, but realistically he had gone stale for Bolton and we did well to get £4m for him. From making his debut back in 1999, Nolan racked up an impressive 341 appearances for Bolton and scored 50 goals - seeing him become Bolton's second highest Premier League goalscorer ever, behind only Kevin Davies. The move gave Nolan a fresh start and he went on to make another 226 Premier League appearances with Newcastle United and West Ham United.
11th January 2008, Nicolas Anelka to Chelsea: £15m
This one hurt, a lot. Anelka was absolutely fantastic for Bolton and scored 21 goals in 53 Premier League games. But the £15m we earned from Chelsea was a pretty good deal considering it was nearly double the then club record £8m we paid for him 18 months previously, even though at 28-years-old he was probably at his prime. But to have had Anelka at our club at all was fantastic, given this was a world-class striker who'd played for Arsenal, Real Madrid and Liverpool.
The next week after selling Anelka we signed Cahill for one third of the fee, then blew the rest of it on Johan Elmander six months later - a player who left on a free transfer at the end of his contract.
So there we have a brief history of Bolton’s dreadful transfer dealings. Are there any deals that stand out for you? Let us know in the Comments section below.