Jimmy Glass already knows what he’ll see when he wakes up today and looks at his phone. “Generally speaking, I always get two messages,” he says, on the 25th anniversary of the goal that catapulted him into legend.

“One will be from my mum, and the other from Roger Lytollis [the former News & Star journalist who ghosted Glass’s autobiography]. Roger’s will say, ‘Happy St Jimmy’s Day’, and my mum will say, ‘Happy May 8th’. So it’s not like the day can ever go past without me thinking about it.”

Just about everything about May 8 transports us back to 1999, when Glass, the goalkeeper on loan from Swindon Town, scored in the final seconds of Carlisle United’s last game of the season to deliver football’s most unlikely and incredible survival. Even the mention of his mum is a throwback, since she was famously called by her boy in the steaming Brunton Park dressing room after the game against Plymouth Argyle before being asked, ‘Guess who scored the winner?’”

Carlisle, Cumbria, and large parts of the world knew the ludicrous answer, and will never forget. The goal's memory, and the love it still provokes among United supporters, have helped sustain the scorer through life’s ups and downs in the quarter-of-a-century since.

The Blues named a bar at Brunton Park after Glass in 2022 and, recalling its official opening, he says: “It was great, and an opportunity to bring my wife [Natasha] up. She had never been to Carlisle, and didn’t really appreciate how famous I was there – or the love I get.

“After opening the bar, we went to the club shop, and some guy rolled up his sleeve and had a tattoo of me on his arm. At that point she realised that some people really love me in Carlisle…maybe even more than she does!

News and Star: Jimmy Glass with wife Natasha at the official opening of Brunton Park's Glass Bar in 2022Jimmy Glass with wife Natasha at the official opening of Brunton Park's Glass Bar in 2022 (Image: Barbara Abbott)

“The irony is that, over the years when I struggled, the one thing that gave me that elation, and hope, and enjoyment was the goal, and what it meant to so many people. So, without wanting to sound too corny – which my wife would say I am – the reality of Carlisle United is that it’s tattooed on me. All the people who showed me that love over the years are part of the best parts of my life.”

Glass has indeed known difficult times, from the decline of his playing career to the gambling addiction that stalked his post-football life as he reluctantly established a new career as a taxi driver. Yet, having turned 50 last August, United’s hero has found bright and interesting new paths.

He speaks warmly about “amazing” Natasha, his second wife, and the two children, Jack and Ella, he had with first wife Louise and who are now 22. In football, a sustained spell back in the game involved eight years as a player liaison officer with AFC Bournemouth, before last year diverting onto a new course.

Glass today is general manager of Wimborne Town, a non-league club in with aspirations. On April 27, a 3-1 victory against Melksham secured the Southern League Division One South title. It meant that, 25 years on from saving United, Glass was celebrating again.

“I couldn’t be there myself, because I was busy organising a youth tournament for 90 clubs at our ground," he says. "So I didn’t really get a chance to get in with the festivities. I had a couple of beers with them once they got back from Melksham, but that was all, and I was ok with that.

“I'm not in the job for the glory of being there and holding up the trophies. I’ve had enough glory in my life. I'm actually there to build a football club.”

Glass was approached to join Wimborne after conversations with Martin Higgins, a financier who in 2021 was involved in a takeover of the club. Glass had spoken to Higgins about the prospects of helping his work with players at Bournemouth. The businessman was not interested in that proposition, but then spoke to Glass about Wimborne.

“He was never a massive football fan, but his daughter plays, and a couple of guys from his company had taken him to Wimborne – and he just got hooked.”

Glass was open to leaving Bournemouth, after changes to the set-up following the Eddie Howe era. “So after our conversation and a bit of to-ing and fro-ing, I've been in there since July last year as general manager.

“My role is just that – it’s general. It’s to basically take the club and elevate it. The four or five-year plan is to get to the National League South, potentially National League.

“When I handed my notice in at Bournemouth after eight years, it came as a shock to quite a few people. To many I had the perfect job. But I just needed something different. And that's what Wimborne Town offered in a much smaller way. Eight leagues below the Premier League….every time I say that out loud I have a little shiver.

“But after everything I’ve experienced with football, it gave me the opportunity to find out whether my thoughts and my feelings about the game would be successful, when I put them into practice.”

Glass, who says Wimborne’s facilities are equipped for levels higher than the Step 3 tier they are about to join, has long been curious about the game’s workings. He says his involvement at executive level now scratches a certain itch.

News and Star: Phil Rigby's famous picture of Jimmy Glass's legendary goal for Carlisle against Plymouth on May 8, 1999Phil Rigby's famous picture of Jimmy Glass's legendary goal for Carlisle against Plymouth on May 8, 1999 (Image: Phil Rigby)

“You probably won't remember this, but in the early-2000s, when Michael Knighton still had Carlisle, I actually tried to muster up some enthusiasm from local businessmen," he says. "The Carlisle Glass guy, Steve Pattison. Even Fred Story. I went to see Brian Scowcroft in Kendal.

“Knighton wouldn't sell to any of the local businessmen, because they all hated him. So I was trying to drum up the idea of me fronting a consortium. I thought Knighton would love the media frenzy of it – the story of the goalie coming back, saving the club and then buying the club. 

"And you know what? It had some legs. We talked to Scowcroft about moving the club up to Kingmoor Park. He would build a stadium, potentially, if he could get some permission to build some retail units. I know fans love Brunton Park, but the club had been struggling for years and needed some sort of new mindset and thrust.

“But what happened – and what usually happens – is the old local businessmen closed ranks. ‘Who does this bloke think he is? Off you trot, Jimmy’. Because they all want their piece of the pie. And then for the next 20 years, you saw Carlisle not particularly grow or develop.

“So the reality was, I was thinking about things like this 20 years ago. And that in itself probably put me off even more, and that's why I stepped away from the game such a long time. It was only really Ed [Howe] being successful at Bournemouth that made me want to go back into football.”

Glass says there is a plan at Wimborne to grow their revenue and build more facilities, as well as nurture their academy, boost their commercial potential and make marginal gains in a way inspired by his old team-mate Howe’s legacy at Bournemouth – and which, he says, is at odds with much else that he experienced in the game.

“Many clubs – and you could probably say the same for Carlisle over the years – have been run by fans who, although they might have a good business brain, still make fan decisions,” he says. “And that's why clubs don't succeed. You need to be objective in your thinking.

“That's what it should have been like 25 years ago. It shouldn't have been about all these lunatic, emotional managers deciding things based on how they felt that particular day. It should be best practice.

“If you're going to take responsibility for a football club, and a football club's a beautiful thing, it's not about who's in charge or who owns it or who's playing for it. Everybody is just a custodian for that moment of its history. And everyone has to respect that and not make it about them.”

News and Star: Glass said his ideas about the workings of football go back more than 20 years, when he tried to front a consortium to buy Carlisle United from Michael KnightonGlass said his ideas about the workings of football go back more than 20 years, when he tried to front a consortium to buy Carlisle United from Michael Knighton (Image: News & Star)

Glass says this vocation intrigues him more than managing or coaching – jobs he has never pursued. “Although I like to talk about football, I don't like to get too in-depth. I'm a bit more basic when it comes to the tactics of football and some of the fundamentals of it.

“Also, I feel that I didn't fulfil my promise as a goalkeeper or as a footballer. I didn't really achieve what I should have achieved. I know that sounds daft when we're here to talk about a goal I scored 25 years ago. But if I see a ball, even now, I want to score it or save it. I don't really want to talk about it.”

Glass says his player liaison spell at Bournemouth helped “get rid of some of the ghosts” he carried from those unfulfilled professional days, which ended at 27, just two years after his Carlisle goal. At times, back with the Cherries, he would join in sessions. “I had a chance to put my gloves on and train when they needed an extra goalie. So I'm diving around in goal with Premier League strikers and still making great saves, and being good enough to be involved.

“If I look back, I was a good enough goalkeeper. I just think, mentally, that I wasn’t in the right place to deal with the professional game. That hurt me. That’s where the gambling came from, and the years of feeling lost. Even though there was plenty wrong with football, and the way it was being delivered, I realise there were things I should have done better. I didn’t recognise that I should have just focused on myself, being the best version of myself.”

Without the “negativity and distractions” that Glass says brought him down, he would not have written his name into history at Carlisle, who were then on the brink of relegation to non-league and, having sold their main goalkeeper and then seen a loan replacement recalled, left desperate for an emergency stand-in for their final three games of 1998/99.

“People ask, ‘Would you swap your goal for a 500-game Premier League career?’” he says. “The romantic in me says no. But the pragmatic, logical side of me would say, ‘Actually, if I’m honest, I’ve had to struggle through life…’ Don’t get me wrong, I’m not poor. But I’ve not had the riches and luxuries. I’ve had to work 17-hour shifts in my taxi and clean up sick at 4am, and all the downsides that come with that.

“Could I have made the most of my opportunity as a goalkeeper? In hindsight, I’d have loved to. If that meant I wasn’t in a position to come to Carlisle at 25 to fill a hole that nobody wanted to fill, and score the goal, then I’d be lying to say I wouldn't have enjoyed that. I’d love to have had a long Premier League career, and be sat on my yacht in Marbella, playing golf every day…”

Glass’s reflections are, though, layered, and he certainly does not regret doing what he did on May 8, 1999. The flipside of being a goalkeeper for hire that spring is that, “I could have had that Premier League career but then been forgotten a couple of generations later.

News and Star: Glass says the love of United fans over the last 25 years has helped him through life's ups and downsGlass says the love of United fans over the last 25 years has helped him through life's ups and downs (Image: Barbara Abbott)

“The beauty of the goal is that it’s given me a way where I’ll never be forgotten. All you really do in life is leave memories. If football’s still going, if it’s still the greatest sport on earth in generations to come, my children’s children’s children might remember me that long-lost, great-great-great grandfather who scored a goal for Carlisle.”

The goal - that iconic finish at Brunton Park's Waterworks end, which spared Carlisle a bleak fate and relegated Scarborough instead - has accompanied him through recent life, whether that be Howe channelling its profound qualities by asking Glass to give a talk to the Bournemouth players before the last game of the 2019/20 season, or the more jovial encounters he has with it.

“Everyone always takes the **** out of me for talking about it. But I never bring it up! It’s only ever when someone asks me about it. When I was hosting at Bournemouth at the top floor restaurant, I’d always start one of my quiz questions with ‘Which goalkeeper scored…’ and the whole room would be like, ‘He’s at it again!'. And the answer would be Peter Schmeichel or something...

“It’s offered so many different emotions over the years. The fact it’s a quarter of a century now is just insane. The truth of the matter is the goal represents the ideal that anything can happen in football. I came to Carlisle for three games with the right intentions to try and help the football club, and I was rewarded for my efforts with the unbelievable last 25 years of memories and pleasure.”

Glass has just about eased away from the idea of trying to revive his playing past, having undergone spinal surgery in 2022. “I got back fit again, and there was this charity game at Bournemouth which I played in. I made some great saves, and for me that was enough. As far as goalkeeping goes, I’m done...because I’ve got standards. I’m 50 now, and I don’t want to dive over a ball or not react properly.

“But occasionally, if there’s a veterans’ game, I’ll have a turnout at central defence or something. I’d love to play up front still but haven’t got that turn of pace any more and I don’t like it. But I’ll always sneak a goal. I’ll always find a goal from somewhere.

“I make my wife and mum laugh when I say I’m going to play in another vets' game. They say, ‘Really?’ I say, ‘Yeah – I’ve got one more goal in me…”

**This afternoon the News & Star will be reliving every moment of May 8, 1999 as it happened - check out our special live blog from 2.30pm**