The pacey striker has spent the last eight seasons in non-league, but is still plying his trade at a high level with Alfreton Town, three divisions below the club where it all began.
Spireites brought the Sheffield-lad through their youth set up, and in April 2006 handed him a two-year professional contract.
Having worked on his game from the age of eight with a single minded determination that he was going to make it as a footballer, this was Jackson’s dream come true.
Buxton beef up with new quartet - and more could be on the way
Buxton manager Jamie Vermiglio happy with opening day point at Peterborough Sports
Buxton are held by 10-men Peterborough Sports in historic first game at National League North level
Commonwealth Games glory for Buxton swim ace Abbie Wood with four medals in Birmingham
Rebuild will take time says New Mills joint manager Dave Birch after defeat double
But his time at Chesterfield, while still a source of pride, unravelled in tragic circumstances.
Looking back, the 29-year-old recalls a difficult period in his life, not just his career.
“Signing a two-year pro contract was every boy’s dream, that’s what you work for from eight years old,” he said.
“But it didn’t go to plan really.
“There were circumstances behind the scenes that weren’t ideal.
“I lost my mum and then the club made me move over there, which probably wasn’t a good idea for me, it just didn’t work out.
“I wasn’t getting looked after like I thought I should have, the club made it more difficult and I had a manager who wasn’t really great with me at all.
“I look back and now and think I could have been helped a lot more.”
Jackson did, however, achieve what so few young footballers manage to do – he broke into the senior side.
And he has no real regrets.
“I did play a few games, mostly off the bench for a few minutes.
“I loved playing in front of the crowds and remember a few games, like Swansea away where I played quite well coming off the bench, and I remember a Forest game.
“My debut at Port Vale away was a highlight.
“I look back and I know people might think things about why it didn’t work out, but I’m proud of myself for doing my best I could in the circumstances, and I’m proud of what I did achieve, something so many people haven’t.
“I don’t really have any regrets, I tried my best – there are people who might think I did something wrong, but I didn’t do anything I wasn’t supposed to do.”
Having gone out on loan to non-league Matlock during his time at Chesterfield, it seemed natural that he would begin his post-Spireites life at Causeway Lane.
This too was an ill-fated move that ended in a cancelled contract, and a York City deal that fell through.
“I signed for Matlock under the agreement that if someone from a higher league came in for me, I would be allowed to go,” he said.
“The new manager came in and one of the first things I spoke to him about was that agreement, and he said it was no problem.
“I was offered a trial at York, to go and do pre-season with them, and the manager again said it wasn’t a problem, I should see how it went.
“I did pre-season at York and was offered a contract, but I got a call saying Matlock had asked for a lot of money for me – and I don’t blame them for asking, I understand they wanted compensation – but it was disappointing, and after that the move to York fell through.
“I was released three months later by Matlock, but the chance had gone.”
A short stint with Sheffield FC followed, and then the first of three spells at Worksop Town.
For the first time, Jackson felt at home with a football club, and Worksop reaped the rewards as he made 123 appearances and scored 40 goals – many of them spectacular.
“It’s just a good family club, there were good people involved, and it was a good platform to go and play.”
Jackson played a big part in Worksop’s first piece of silverware for nine years, scoring twice at Hillsborough as Tigers beat local rivals Frickley Athletic.
But the next two seasons weren’t so successful, bouncing around non-league with Bradford Park Avenue, Belper Town, Grantham Town and Worksop Town again.
From the outside it might have looked like Jackson would continue to do the rounds in the Northern Premier League, or lower, but instead his career got a much needed shot in the arm.
He spent the summer of 2014 with Conference Premier club Alfreton, but when no deal was forthcoming, their division rivals Halifax swooped in with a unique opportunity that involved facing off against his brother, former England international Kevin Davies.
“Halifax asked me to go for a trial game against Preston, who my brother played for at the time.
“It had always been in my mind to play against him, so it was a no brainer really.
“Halifax gave me a contract straight after that game.”
It was a big leap, from the Evo-Stik Northern Premier to the Conference Premier, but Jackson insists he’s always found life tougher the lower down the football pyramid he has gone.
“Non-league is difficult, and I find that the higher I’ve played, the easier it is.
“The lower I’ve gone, the harder I’ve found it and normally you have to prove yourself at one level to move on to the next.”
Last season was an enjoyable one for Jackson, and he feels he made a positive impact in the games he played.
Negotiations to stay at the Shay didn’t come to frution however, and he found himself moving on again – but not before picking up an accolade.
“I got Goal of the Season for a last minute winner against Braintree and that was a proud moment,” he said.
“The circumstances of it, I started the move and finished it, that goal stands out as a highlight for me.
“I loved it there. They’ve struggled a bit this season but hopefully they’ll pull through and stay up.”
This season, Jackson finds himself in the National League North with Nicky Law’s Alfreton Town.
And they’ve hit a rich vein of form.
“It’s been an up and down season as they all are, but we’re going strong at the minute.
“I’ve just been waiting for a chance to play how I want to, and get in the team.
“It’s been hard work at times but we’re on a good run and hopefully that will continue.”
At the ripe old age of 29, Jackson is working harder than ever to stay in shape, an aspect of the game he says he’s never shirked.
He’s also working away from the game, and believes he was one of the lucky ones who had time to adjust to life in the real world after an early release from the professional game, unlike those who exit the full-time ranks in later life.
“It’s such a hard transition, emotionally, having the idea that you’re not going to be a professional footballer anymore, it’s very difficult to come to terms with.
“I didn’t get a job when I was at Matlock for a while, I thought that was my giving up on my dream.
“People in non-league work hard in jobs and then go off to football, but I do feel sorry for lads who are dropped from professional clubs later.
“If you drop out from 16 to 19 you still have plenty of time to get a career together.
“I work with disabled people through the week, I do a couple of night shifts and it works well with my football, I can move things around.
“I enjoy it, it’s got that feel good factor, as football does, and I don’t see why I wouldn’t carry on with it and look to progress after football.”
While Jackson is still playing a good game, the other footballer in the family is now talking one.
His brother, also a striker, forged a successful career as a professional with Chesterfield, Southampton, Blackburn Rovers, Millwall, Bolton Wanderers and Preston North End.
He also picked up an England cap.
There has never been any jealous glances from the younger sibling however.
“We’ve always been fairly close, so there’s never been anything other than pride in what he has achieved,” said Jackson.
“It’s brilliant, to make such a long career and achieve what he achieved, to be spoken about as highly as he is.
“He wasn’t the greatest technically, but he made a great career out of what he did have, and worked very hard for it.
“It’s always been difficult for us to get to each other’s games, both playing on Saturdays, and now he’s retired he’s working a lot with punditry, but as much as we can we keep in contact.”
Davies hasn’t been the only positive influence in Jackson’s career, with two managers and one team-mate in particular standing out.
“In terms of the best managers I’d have to say Neil Aspin at Halifax and Martin McIntosh at Worksop.
“I’ve had too many managers that gave too many rollickings, and that just doesn’t really inspire me.
“And as for team-mates, if I don’t say Adam Smith he will get angry with me – we’re best mates.”
All this reflecting on the past comes with an important footnote – Jackson says he’s far from done with the game yet.
Although he may wake up a little more achey than in his early 20s, the front man says extra stretching and gym work keeps him in shape.
And experience wins over youthful zeal.
“It’s all about body management, I know what I need to do through the week to get myself into a position to play.
“I’m feeling a bit of stiffness creeping in, more than I used to but it’s more about attitude, you’ve got to give yourself the best chance of playing.
“And I want to play for as long as I can, football is still a major priority in my life.”