Published28th May 2026, 08:00 BST
This Sunday, he will turn out back home in Ireland in a title decider in the Wicklow Sunday League for St Anthony’s against Ashford Rovers.
Time may pass, but for footballers, some things never change. The appeal of the game never wanes. And at the grand not-so-old age of 40, O’Connor is still going strong!
His footballing story is one of both joy and pain. Like so many. A tale of years of blood, sweat and tears to achieve his lofty aspirations, and playing for Wolves in the Championship.
To the agony of a complex and lengthy injury nightmare from which he would never be the same again, nor reach anything like the same level again.
A couple of decades on, the affable Dubliner remains - as he always was - calm and philosophical.
“You have to work incredibly hard in football to make it all the way through to play for a first team,” O’Connor tells the Express & Star.
“But then it becomes such a short spell, injuries arrive and it’s absolutely devastating.
“I always feel I could have kicked on and stayed in the team and who knows where my career would have gone if that happened.
“That’s a question we will never know, and football can be a cruel game at times, that’s the way it goes.”
There was always a grounding and perspective to O’Connor who worked so hard to earn his chance at Molineux. His dedication and commitment, combined with his ability to win a tackle, pick a pass and generally get around the pitch, made him a perfect arrival to the starting line-up under McCarthy. He was his type of player, especially during that hurried summer of 2006, when the new boss had less than two weeks to prepare for the start of the season.
It was a talent and attitude forged over many years learning his footballing trade back home in Ireland which secured O’Connor a place within Wolves’ Academy.
Starting out at the age of six with Wolfe Tone and District Youth Club, he was one of three footballing brothers, of whom the eldest – James – was first to cross the water for a successful trial with Stoke City.
That was a step which motivated O’Connor to push for similar, and a move to St Joseph’s Boys in Dublin and the more competitive Dublin League also led to an increase in the number of scouts at games.
At 14, he travelled over for his first trial with Newcastle, who were keen, but on thinking there wasn’t the best chance of progression on Tyneside he decided against. Stoke City followed, who were also keen, but, whilst O’Connor was mulling over that potential switch, Wolves also made their move.
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AMA
The club’s legendary Irish scout Willie Byrne had actually been the talent spotter who recruited James to Stoke, and, now working for Wolves, it seemed a natural fit for Kevin to follow suit but head to Molineux instead of the Britannia.
“The first time I met Willie he was such a gentleman and I had a really good week’s trial when I came over,” O’Connor recalls.
“Chris Evans was in charge of the Academy, and Tony Lacey, who knew James from his time with Stoke, was playing a key role.
“I already had a bit of a soft spot for Wolves, and the overall feel of the club was so much better than the others. There was a real genuineness to everyone and wanting to look after me.
“It was around that time that I made my debut for the Republic of Ireland junior side at the age of 15, and Chris, Willie and Tony all came over to watch.
“After that they came to my Mum and Dad’s house and said how much they wanted to sign me – they really made an effort.
“It just felt right and I was delighted to sign, and straightaway Wolves paid for my gym membership and put me on a programme to work on before I came over full-time at the age of 16.”
O’Connor relished his time within the Academy. In digs with landlords Chris and Alex McNamee, his football flourished under coaches Keith Downing and John Perkins, and later Terry Connor, for whom he would captain the reserve team.
Being away from home for the first time brought challenges. “When you are 16 you think you know everything, but you don’t,” he admits.
Having James a couple of bus rides away in Stoke and then even closer at West Bromwich Albion helped. His elder brother was several years ahead in his footballing journey and could guide his sibling through the processes and the pitfalls.
But, as with every young player aspiring to make the first team, so much then depends on the manager.
Under Glenn Hoddle, despite regularly training with the first team and taking the armband for the reserves, O’Connor never felt that a chance would come. No regret or bitterness, as he fully appreciates selections are always up to the manager.
On being sent on loan to Stockport in League Two, he not only helped them clinch survival, but notched his first senior goal, against Shrewsbury.
Whose goalkeeper, until this week unknown to O’Connor, was none other than Joe Hart.
In terms of Wolves, after Hoddle handed in his resignation with the 2006/07 campaign just weeks away, things very quickly changed.
“I felt I was playing great football in training and the reserves, but I just wasn’t in Glenn’s plans and that’s fine, it happens to most players throughout a career,” O’Connor admits.
“The loan spell was great because there is a big gap between reserve and first team football so that gave me valuable experience.
“They were fighting to stay up which we managed to achieve and it helped that I felt I was able to contribute to the group.
“I remember on the Saturday Glenn resigned and then on the Monday we were going to a pre-season training camp in Spain.
“And immediately, for me, things felt different.
“I had the utmost respect for Terry, and when he and Stuart Gray took the team on that trip, I suddenly felt like a first team player.
“Up until then, every time there were games in training and the bibs were handed out, I knew I’d be in the team up against the first team players, but now I was starting to get chances.
“It shows how quickly football can change and then, when Mick McCarthy came in, I got a good vibe right from the off.
“The big thing about Mick was that he is always straight talking, and I think my style of play suited what he was looking for.
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Dave Bagnall
“I’d be a hard worker, I’d get box to box, and, in the pre-season, I was always fit.
“There were a lot of changes that summer and Mick quickly had to build a squad, and I was fortunate to be a part of it.”
He was indeed. For the first game of what proved to be a transformative managerial reign, McCarthy picked O’Connor in his midfield, alongside recent signing and future captain Karl Henry.
It was Plymouth away, and very much a patched-up side given who so many senior figures had departed prior to Hoddle’s exit, but O’Connor grasped his opportunity.
And just 90 seconds into the second half, with Wolves a goal down, O’Connor’s shot looped up off defender Matias Kouo-Doumbe and into the back of the net, ultimately securing a decent point.
“It’s nearly 20 years ago now, but I still very much remember standing in the tunnel at Plymouth,” says O’Connor.
“There was a decent crowd there and I can remember the noise as we were waiting to go out.
“As I have said, you work so hard to try and get a chance, and it’s always a dream when you have come through the Academy and reserves to make it into the first team.
“When it happens, it’s quite surreal, but at the same time you don’t sit back and depend on that, you have to go out and do a job.
“And the goal was another incredible moment.
“On paper it might have been taken away from me and given as an own goal, but at the time, just being able to celebrate as if it was mine with all the lads around me, was amazing.”
Current Wolves Head Coach Rob Edwards came off the bench on that afternoon, as he did for O’Connor’s following two starts at Molineux, against Ipswich and Preston.
Those provided two more special moments, playing on home soil and with his family over to watch, including beating Ipswich 1-0 despite Carl Cort’s first half sending off, before taking the lead against Preston only to lose 3-1.
A week which dreams are made of, but sadly, they were to be followed by a nightmare.
O’Connor, on cloud nine following his first team breakthrough, was quickly brought straight back down to earth when suffering a hamstring injury.
Initially put down to an overload of playing his first three first team games in such a short space of time, even with rest and treatment there was no improvement, with various scans failing to fully identify the problem.
With the injury finally diagnosed as being linked to a piece of bone rubbing on his sciatic nerve, O’Connor was sent to Finland for surgery, after which he made good progress until suffering one of those freak accidents that seem to afflict footballers from time to time.
In trying to help his partner bring in the shopping on a rainy day, he slipped whilst jumping on his drive from gravel onto grass, falling into a hamstring stretch which led to further problems.
After a further period of rest failed to alleviate the issue, he returned to Finland where the surgeon discovered that the additional slip had actually ripped the hamstring from the bone.
“It was such a difficult time,” O’Connor admits.
“Prior to the first surgery, even when I was driving and just using the clutch, I was getting shooting pains into my toes and pins and needles, and I couldn’t sleep properly.
“Then all seemed fine again before the slip, but after the second surgery I tried again to get back.
“I had been really pushing myself because the club were deciding about an option year on my contract, but Mick was great, telling me I was getting the extra year and to take my time getting back.
“That was always the type of manager that Mick was, but when it came to a year later, and I was still struggling, the decision was a no-brainer because they couldn’t give a deal to someone who just hadn’t played.”
There was more bad luck still ahead. After a trial at Port Vale which he didn’t get a great ‘feel for’, O’Connor had impressed at Walsall and got to the stage of talking potential terms, until damaging the medial ligaments in his knee in training, prompting another lengthy absence.
“By then it had got to the stage where I was still caught trying to chase the dream, but the reality was I wasn’t getting paid anymore,” he admits.
“I had a family with a young son, a mortgage to pay, and the reality of life set in.
“I had to finish playing professionally, in December of 2008, just over a couple of years since I had made my Wolves debut.
“Yet I couldn’t allow myself to dwell on it all too much, and tried my best to accept it, otherwise I don’t think I’d have been able to bounce back.
“The pressure was on, and it was time to try and crack on and see where another opportunity might come.”
O’Connor would spend a year completely away from football, trying to get any sort of job, albeit finding recruiters preferred to talk to him about life at Molineux rather than his potential work prospects!
Eventually he landed a role as a personal trainer, with thanks to the PFA for funding the training, working out of the David Lloyd Centre at Brierley Hill.
This dovetailed with playing non-league for Telford and then Worcester, before, thanks to other footballing brother Danny, O’Connor was alerted to the possibility of returning back to play in Ireland.
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Second from the left on the back row, O'Connor as a number ten with St Anthony's in the Wicklow Sunday League
Eventually that led to securing a semi-professional contract playing alongside Danny under Pat Devlin at his hometown Bray Wanderers, which included a job working in air conditioning on building sites.
“Having said that, I’m in no way a handyman, I was gifted with my feet rather than my hands,” O’Connor laughs.
With Bray, he scored the play-off winning goal which preserved their Premier Division status and denied opponents Longford Town promotion – and then immediately went and signed for Longford!
During four years with Longford, he made up for that play-off goal by helping them to promotion via the First Division title, before finally hanging up his boots in 2017.
By this time, he had changed his working life again, following some more advice from Danny and entering the world of finance.
He had to return to studying to complete the Irish Leaving Certificate which he had missed out on due to heading to Wolves at 16, and has since spent over a decade in the industry, now bringing in new mortgage business for EBS Greystones in Wicklow.
Life back home in Ireland is good. O’Connor married wife Leanne 18 months ago, and has an 18-year-old son Darragh from a former partner, with whom all is still very amicable, back in Wolverhampton.
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In the day job, working in finance with brother Danny at EBS Greystones
He enjoys regular trips back to see Darragh, also a keen footballer, and enjoys catching up with Wolves fans, wherever they may be!
And then there is the return to competitive football. In January of this year, after a lengthy period of dipping his toe in either five or seven-a-sides, he started playing Sunday League for St Anthony’s.
Now operating as a number ten, “so the younger lads in the team can do my running”, he’ll be hoping to deliver a positive impact in the winner-takes-all finale at Finn Park this weekend.
Twenty years on, O’Connor is ready to savour that big game feeling all over again!
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