“You’d literally be playing out here and getting scraped up off the floor.” Bradley Woods-Garness is standing a few yards from one of the north London pitches that, when he was a youngster, tested mettle as much as skill. The five-a-side surface at Elthorne Park is now made of artificial turf, a far cry from the concrete that would shudder the bones of the Corinthian-Casuals forward and those who joined him. “There’d be scars all over your knees,” he says. “But we loved it.”

It is a chilly Sunday morning and, just behind him, a new generation is going through its own rite of footballing passage. Woods-Garness has returned with five of his oldest friends, all of whom cut their teeth in uncompromising surroundings here and at other venues around Islington. Each of them still lives locally. They could never have imagined it but all of them are international footballers now, playing for the same side, and they stand on the verge of something extraordinary.

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If Montserrat defeat Cayman Islands in the early hours of Saturday then, with favourable results elsewhere, the tiny Caribbean island’s team will qualify for their first Concacaf Gold Cup. They are ranked 200th in the world but a core of players who grew up a few streets apart have helped turn their fortunes round.

Recruitment for the national team always leant upon word of mouth. Thousands of Montserratians relocated to the UK during the 20th century, Windrush arrivals followed by those who were displaced by the Soufrière Hills volcano’s catastrophic eruption between 1995 and 1997. The side was mainly staffed by their descendants, usually England-born and playing on the non-league circuit. That has not changed much but the way things fell into place for the current crop makes remarkable listening.

“I literally started asking everyone I knew who played football at any level: ‘Do you have any Montserrat in you?’” Dean Mason is among three of the group who play for the National League side Maidenhead United. He began representing Montserrat in 2012 – qualifying through his paternal grandmother, a Windrush settler – after striking up a friendship with the now Sweden-based player Alex Dyer; he and Woods-Garness were teammates at Canvey Island then and, en route to a match, he mentioned his call-up. “I’m from Montserrat too,” Woods-Garness replied. When their mutual astonishment had subsided, they set to work on signing him up with the British protectorate’s FA.

Facebook Twitter Pinterest Adrian Clifton juggles a football as his teammates look on. Photograph: Jonny Weeks/The Guardian

The pair discovered a squad accustomed to crushing defeats and sought to strengthen it. No stone was left unturned: social media were scoured, friends of friends petitioned. Sol Henry, a veteran of the local non-league scene and friend from those bruising kickabouts, was enlisted during a night of tenpin bowling in 2014 and found himself flying to a Caribbean Cup tie against the US Virgin Islands within days.

Adrian Clifton says he saw an Instagram post showing his companions on a beach and thought: “What’s going on?” He would make his debut in March 2015, during a World Cup qualifier with Curaçao. James Comley, who completes the Maidenhead contingent with Clifton, had believed his grandfather hailed from St Lucia but, after casually telling his father that Mason and company were travelling with Montserrat, was amazed to be put straight. He would also begin against Curaçao. Last year Comley’s younger brother Brandon, the Colchester United midfielder, also won his first cap.

Quick guide The men making history for Montserrat Show Hide Golden boys? Craig Braham-Barrett Welling United Corrin Brooks-Meade free agent, most recently with Montana in Bulgaria Dajour Buffonge Congleton Town Adrian Clifton Maidenhead United Brandon Comley Colchester United James Comley Maidenhead United Alex Dyer Lillestrom, on loan from Elfsborg Marvin Farrell free agent, previously with Beckenham Town Sol Henry free agent, most recently with Horsham YMCA Micah Hilton PC United, Montserrat Dean Mason Maidenhead United Massiah McDonald Rushall Olympic Terrell Miller Redbridge Joey Taylor Hythe Town Lyle Taylor Charlton Athletic

Spencer Weir-Daley Gresley FC

Bradley Woods-Garness Corinthian Casuals Michael Williams free agent, most recently with Rushall Olympic

The deep-set bond between all six is clear: the ribbing and in-jokes barely let up but there is a tenderness, a sensitivity, about their interactions too. None of them envisaged this during those days taking kicks on the gravel. Mason saw the new-look team take shape and began to think: “We can definitely do something here.” A much-improved Montserrat ran Curaçao – a formidable side packed with talent from the Dutch leagues – close in that tie; it was a precursor of what they have achieved since but none of them knew, at the time, that the team would not play again for three and a half years.

“People forgot about us,” Mason says. “It was horrible. We stuck together and kept a WhatsApp group going but I felt it was just turning into a whole lot of sarcastic comments. It was like: ‘We’re never going to play together again so we might as well meet up and go to Topgolf.’”

They now understand we’re not here for money and just want to give something back Bradley Woods-Garness

Their adventure appeared to be over as soon as it had started. Montserrat had contested only 34 games since first playing in 1991, in any case; the resources for regular fixtures beyond World Cup ties were just not there. But Concacaf’s creation of a Uefa-style Nations League transformed everything. Now each team was guaranteed meaningful competition and money to stage it. The top 10 of a 34-team table will join sides such as the USA and Mexico at this summer’s Gold Cup. Montserrat came within seconds of a draw with El Salvador last September; they subsequently beat Belize and Aruba. It creates an opportunity on Grand Cayman that would have seemed impossible in 2002, when they lost 4-0 to Bhutan in the “Other World Cup final” between the globe’s two lowest-ranked teams.

Overseeing Montserrat’s resurgence is Willie Donachie, the former Scotland international and assistant to Joe Royle at various clubs, who became manager last year. James Comley describes him affectionately as “like a Buddha”; the players admire his serenity and man-management, also appreciating how he allows a necessarily self-sufficient bunch their say on tactics. Donachie quickly understood their closeness and, in several cases, grounding at top-flight academies could be harnessed effectively.

Only 5,000 people live on Montserrat and, at first, the newcomers detected some suspicion. “They now understand we’re not here for money and just want to give something back,” Woods-Garness says. “We are winning games, they’re taking to us and enjoying what we do. They can stand up and say: ‘Yeah, you can’t beat our island!”

Facebook Twitter Pinterest Smoke and ash billow from the Soufrière Hills volcano on Montserrat in August 1997. Photograph: Kevin West/Associated Press

The process of connecting their roots has been difficult but important. “Every time my grandad talks about home he always says: ‘Where I’m from in Montserrat ain’t there no more,’” Clifton says. “It’s always been an uncomfortable conversation. So to go there and see what he actually meant with my own eyes, half the island literally empty, one side green, one side ash …” He trails off and the group swap memories of the tours they received, taking in the island’s exclusion zone, upon visiting for the first time. After understanding the devastation that had been wreaked, there was no mistaking what they had committed to.

The hope is others will follow. “We’re just kicking this off,” Clifton says. “It’s only going to get bigger; there’s going to be better players than us coming through.” Montserrat can now afford their own talent detection; the days of scouting for teammates are gone. Lyle Taylor, the Charlton forward, is their highest-profile player but a number of Premier League clubs are producing footballers of Montserratian ancestry and there is optimism that, with continued progress, the temptation to hold out for a call from England will be reduced.

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By the time they sign up, the boys from those neighbourhoods around Elthorne Park may have completed their fairytale. “We’ve created a fear and other teams respect us,” Clifton says. Montserrat must justify a rare “favourites” tag with three points against the Cayman Islands and hope three other results go their way. The permutations are complex but it is not far-fetched. Finishing the job would crown a tale worthy of a film script.

“I don’t think anybody could believe something like this was possible,” Woods-Garness says. “I don’t think they could believe that five, six, seven people from the same area can grow up together and go on to play international football, and be on the verge of making something as big as the Gold Cup. It’s phenomenal.”