Tonight at Old Trafford will herald the biggest 90 minutes – or 120, or maybe more – of the young footballing lives of the aspiring Wolves talents taking to the pitch for the semi-final of the FA Youth Cup.

Victory against Manchester United would take Wolves to a first final in the competition since 1976, which would be at Molineux, accompanied by the subsequent carrot of lifting the trophy for the first time since a sensational Ted Farmer-inspired success against Chelsea in 1958.

Win or lose however, either result will not be decisive one way or the other for the careers of the Wolves Academy class of ’22.

The sheer experience alone will be an invaluable one on that long and arduous journey from the youth ranks to hopefully, one day, following in the footsteps of the illustrious array of talent that has worked its way along the conveyor belt of Wolves Academy over the last three decades or so.

Keane, Smith, Naylor, Robinson, Murray, Lescott, Andrews, Hennessey, Davies, Ikeme, Davis, Price – a lengthy and ability-filled list which doesn’t even scratch the surface of the production line of graduates who have come through and tasted first team football whether at Wolves or elsewhere.

Tough acts to follow, but ones which the likes of Morgan Gibbs-White and Luke Cundle have pursued with plenty of potential in recent times.

And now Steve Davis and his staff and players have done an excellent job navigating a path for the Under-18s to the last four, the first time for Wolves since 2005.

Those two legs of the semi-final against a star-studded Southampton side, including an epic and almost so famous night at Molineux, yielded a group who went on to enjoy plenty of success.

Wayne Hennessey, Mark Davies and Elliott Bennett all went on to play in the Premier League, Stephen Gleeson – like Hennessey and Bennett – became a full international.

Mark Little made 32 senior Wolves appearances and is still going strong with Yeovil, Chris Cornes appeared on the bench for the first team and went on to feature for Port Vale, Lee Collins forged an excellent career with several different clubs.

Martin Riley went on to play in the league with Cheltenham and Mansfield, and there were others who didn’t make it in the English system – such as Gareth Musson, Jonny Taylor and Conor Rafferty – who played at a high level in other countries.

Among that group is also the name of Tommy Stewart, then an ambitious 18-year-old striker, now an ambitious 35-year-old coach, whose wide range of experiences both at Wolves and beyond have played such an integral part of his career, and potential future.

Stewart was a key part of that FA Youth Cup run of 17 years ago.  A different generation.

He wore the number nine shirt as Wolves went into the second leg against a Southampton side 1-0 up from the first which included in its squad the likes of Theo Walcott, Leon Best, David McGoldrick, Adam Lallana, Nathan Dyer and Martin Cranie.  Gareth Bale, slightly younger than those others, was in the squad but not the team.

With an hour on the clock, in front of a fiercely partisan crowd of 8,803, Wolves found themselves 2-0 down on aggregate, before Stewart halved the arrears with

a clinical low drive after running across the edge of the penalty area.

Jordan Fitzpatrick then drew Wolves level, Davies nudged them in front in extra time, but the agony of a late Best goal paved the way for a penalty shootout from which the Saints marched on.

By that point, Stewart had been forced off through an injury of his own, and he is left with mixed memories from such a powerful experience but one which, ultimately, ended in defeat.

“It was a fantastic night and a fantastic build-up to the game,” he recalled this week.

“We were under no illusions, Southampton had so many tremendous players who they had bought into the club and Theo Walcott was the big name – he was getting all the plaudits.

“But for us, John Perkins was doing a great job as our coach and we were certainly ready for what was the biggest game of our lives.

“At that age you take football so seriously, it takes over everything.

“We felt like we were so close to doing something special for the club and our own careers.

“I can still remember the game, full of highs and lows, and so many fans, including my Dad who had flown over from Ireland.

“It was such a great feeling coming on and seeing that ball hit the back of the net to get us right back in the tie.

“And yet, near the end of extra time, I started cramping up.

“I had run myself into the ground, trying to cover every blade of grass to help us get to the final.

“I went up for a header, their guy landed on me, and as soon as I went down, I felt my calf and I knew I couldn’t continue.

“It was such a disappointment the way it ended but it was also such a great run in the competition and something I still remember very fondly.

“But also, when I look back on that game, there is also a sense of, we were so close!

“On another day we might have got luckier and got to the final although there is no guarantee we would have won that.

“I think that run gave all of us a little taste of what was out there but getting that winning feeling, we wanted it more.

“Thankfully I went on to have that fire in my belly that helped go on and win things afterwards.”

Stewart certainly did that.

Upon leaving Wolves he joined Linfield in the Northern Ireland Premiership and helped them to no fewer than five trophies within a couple of years including a couple of league titles and a couple of Irish Cups.

He then moved to Derry City, winning the League of Ireland Cup, before heading south for Shamrock Rovers, lifting the League of Ireland title and the Setanta Sports Cup.

And the foundations of that success, Stewart feels, were in no small part laid at Wolves.

He was a teenage striker banging goals in for Portadown when first coming to the attention of several clubs in England, including several of high calibre.

Manchester United, Tottenham and Sunderland were among those who had expressed an interest before an impressive performance in the Milk Cup saw Wolves enter the fray.

At the time Wolves Academy, headed by Chris Evans and boasting well-respected Irish scouts such as Willie Byrne in the south and Norman Boyd in the north, had enjoyed plenty of success bringing prospective talent across the water, Robbie Keane the perfect example.

After heading over to visit the club, the young Stewart was instantly hooked.

“I fell in love with the club from the moment I arrived,” he recalls.

“Wolves was a club with a lot of promise at the time with aspirations to get into the Premier League and it was something I wanted to be a part of.

“There were a lot of good people there, and having seen someone like Robbie go over and do so well, that was an inspiration.

“They were talking about wanting to give youth a chance, and I was delighted to sign.”

For a spell Stewart would fly over after school on a Friday to play on a Saturday before returning home, eventually signing a full-time scholarship at 16.

In digs with Morris and Maureen Dowling in Pendeford, he settled well, despite the ‘bittersweet’ feeling of being away from his close family, and, on the pitch, made rapid progress.

Top scorer for the youth team, he captained both them and the reserves, but ultimately, feels he perhaps struggled to make that final breakthrough at a time when Wolves, with changing managers through Dave Jones, Glenn Hoddle and Mick McCarthy, were going through something of a tactical transformation.

Stewart made one first team appearance in a friendly at Telford, playing alongside Kenny Miller and finding the net, but more regular senior football would need to be found elsewhere.

“I think I did o-k in those years in the academy but it was a time when football and tactics were changing a little bit,” Stewart explains.

“At the time it was all about a 4-4-2 formation, something I was brought up with and comfortable with but now probably not the best approach if you want to try and dominate a game.

“But I was used to that approach, two up front with a striker flicking it on and a runner in behind, but it changed and trying to become more of a ‘spearhead’ as a striker was a challenge, particularly as I still had some physical development to come.

“The way we started to play at Wolves maybe didn’t suit me from the tactical side, although it was something I learned from and went on to do well in that formation both for clubs and at international level, often on the wing.

“There was also a change in managers, when Glenn Hoddle came in he bought more older and experienced players and I left just before Mick McCarthy, who gave youth an opportunity.

“There was a wee overlapping of strategy and mentality and I fell into that gap of needing more development and not being quite ready.

“It feels a long time ago now when I was at Wolves but I have no regrets and only fond memories of a great start to my career.

“There was a bittersweet feeling in leaving home and leaving my family but it is about making sacrifices and doing them proud, and the club always looked after me well.

“It is still the sort of opportunity which every boy or girl wanting to be a footballer dreams of.”

Stewart certainly pushed on after leaving Wolves, with those individual and team successes during those spells on both sides of the border in Ireland, not to mention playing in Europe.

Hitting the continent including a two-legged tie in the Europa League against a Juventus side boasting the defensive pairing of Leonardo Bonucci and Giorgio Chiellini and Alessandro Del Piero up front.

“Just getting the chance to play senior football in those years was the biggest thing for me, and then obviously winning some trophies topped it off,” Stewart recalls.

“When, as a kid, you experience something of that magnitude with the Youth Cup run at Wolves, it makes you more determined to win and I have been fortunate to have tasted success in various competitions in various cities around the world which I am very proud of.”

And when he says around the world, he means it.

It was back in 2014 that Stewart took the plunge to head to North America and join Sacramento Republic, a new club in the United Soccer League’s third division.

In their very first season, they won their division, and Stewart, once again, was top scorer.

“I was there for three seasons and it was such a great experience,” explains Stewart, who while in America also caught up with lifelong Wolves fan and successful writer Charles Bamforth to be interviewed for the Wolves Heroes website.

“We would get 20,000 turning up every week which was an incredible feeling, and a reminder of the support Wolves had with that amount of fans and stature of occasion.

“It was something unique – I would never be able to experience it again, certainly not as a player, but maybe one day as a coach?

“That is another part of my career which I look back on so fondly – it just went way too quick!

“It helped put football on the map in California, and was almost like a dream, so surreal.”

California dreaming indeed.  Without a winter’s day.

And it was also an experience enhanced by a visit from one of the greatest strikers to have ever played the game – Didier Drogba.

As Stewart explains.

“I think Drogba was struggling with his knee when he was at Montreal and needed to get some heat with his treatment as it was freezing over there!

“He came in with us for a few weeks and was such a great lad with a great attitude and one of those people you just react to and respond to straightaway.

“He was such a presence around the place, and someone that everyone could lean on.

“At that stage of my career and being at a newly formed club people were looking to me for experience but when someone like Didier Drogba is around for a few weeks that is a different kettle of fish completely.

“This was a Premier League winner, a Champions League winner, but was someone who was incredibly proud of what he had achieved – rightly so – and was happy to share that information with you.

“And he was also such a humble guy, we’d all go out for dinner and for drinks, and he was a huge person to be around the dressing room for a few weeks, to tap into his insight.”

All those experiences have been invaluable for Stewart, absorbing information, building his knowledge base, watching and learning from others within the game, honing his own coaching strategies and approach.

During his career he has worked under four different international managers – Hoddle at Wolves, current Republic of Ireland manager Stephen Kenny at Derry, former Northern Ireland and current Stoke boss Michael O’Neill at Shamrock, and now, in his present role as a coach with the Northern Ireland Women’s Development set-up, the senior team manager, Kenny Shiels.

Former Wolves and Scotland international defender Jackie McNamara can also be added to that illustrious Who’s Who, during a short spell Stewart enjoyed with Partick Thistle.

Stewart also enjoyed international honours as a player, captaining the Under-21s and amassing 19 appearances, whilst also scoring the only goal for the Under-19s against Germany in the European Championships of 2005.

Having first started developing his coaching skills all those years back as a scholar at Wolves, and getting involved further during his spell in America, Stewart now has his UEFA A-Licence and has a long-term ambition to forge a successful second career within football.

“When you think of my experiences, and all those managers, everything I have learned along the way has played a part to get me to where I am now, working with Northern Ireland’s Women’s Development squad,” he says.

“I feel very lucky and blessed to have played for the teams that I have.

“Working with different managers, different styles, and developing your own way of treating players and those players who maybe aren’t quite ready who need a wee bit more help or time to develop physically and tactically.

“There are so many different variables, but I really feel like I have learned so much that I can pass on and help both individual players and teams.

“Coaching is not the easiest job to get into, and opportunities can be limited, but I am really enjoying what I am doing at the moment.

“It still feels like I am learning the trade and I want to make sure I am across everything, working with boys and girls players, men and women, to build up respect and experience.

“That is what I really want to do for the next couple of years, and then really push on, although if any other opportunities come up quicker then I feel comfortable and confident with what I have learned so far.

“I am not silly enough to think the game ever stops changing and I know I will have to change with it.”

What has also perhaps changed within coaching and football in general over recent years has been an increasing focus on players’ welfare not just on the pitch, but off it.

Discussions around mental health have, thankfully, become far more prevalent, and Stewart was among former team-mates of Lee Collins, who played so well up against Walcott in those 2005 Youth Cup semi-finals, left devastated when he took his own life last year.

By that stage Stewart, clearly a rounded character and a deep thinker beyond just what happens on a football pitch, had already tried to make his own contribution to supporting people with their mental health, by turning to music.

In memory of his mother Louise, who had sadly passed away after a short illness, and during lockdown, when many people were struggling, he actually wrote and recorded a song.

‘I’m A Better Man’, designed to encourage more people to open up on their emotions and ask for help, raised almost £1,000 for the Stephen Clements Foundation supporting several mental health charities and initiatives. It’s a powerful song, and a powerful message.

“Losing my mother was the force and the motivation behind the song, the inspiration, and writing it helped me process everything that was going on after her passing,” he explains.

“There was also a message behind it, as unfortunately a lot of men in sport have suffered with depression and some have committed suicide.

“It can sometimes be difficult to speak out, but just because someone is successful in sport, they are not bulletproof, and need support off the pitch as well as on.

“I had the idea and reached out to an old friend from a music company I knew from my time with Larne and he thought it was a great idea when he heard it.

“It’s had a good reaction and has ended up being played across the world and the message remains strong: ‘Don’t give up and don’t give in,’ which is something I firmly believe.

“Hopefully anyone who is going through something can maybe hear it or just reach out as we all have to help each other.

“I have learned a lot that for everything to be right it has to be right in life as well as in football and I would like to think I have always been someone who cares for my colleagues as a player and as a coach.

“Football is a brilliant sport, and it’s an entertainment business but at the end of the day we are all people – and it is important we always keep that human touch.”

It’s a strong message, and one Stewart tells well, and one that remains pertinent to young footballers trying to make their way and overcoming setbacks as they do.

It is why clubs now make sure they look after the mental wellbeing of players just as much as the physical, and why Wolves Academy now have a player care team, so that those involved know that while tonight is important, it’s not the be-all and end-all.

“There is a really big platform for the lads to play at Old Trafford, and the motivation that if they can take Manchester United down then there will be even more opportunities ahead,” says Stewart.

“Football is the biggest sport in the world, so regardless of the result and how their Wolves careers may go, there are so many doors which can open and different avenues to follow, whether that is playing or coaching.

“It is always important to learn something from a game like this – to go in and give it 100 per cent and be ready to give your absolute all for the badge.

“It’s why you play football, for games like this, and to try and win things, to do your club and your city proud.

“All you can give is your best, and I will be watching on from afar and hoping the Wolves lads go one step further than we did!”

Whatever happens this evening Stewart is a shining example of the many different routes a career can take and the importance of being ready to make the most of those opportunities when they come along. Wherever they may be.

And by the way. The last time Wolves won the FA Youth Cup when Farmer scored four as Wolves overcame a 5-1 first leg deficit to win 6-1 at Molineux and 7-6 on aggregate.  

The semi-final opponents that year? Manchester United.