• Lee Bowyer was appointed Montserrat coach in September 2023

• Former England international believes nation can reach FIFA World Cup 26

• Montserrat will face Panama, Nicaragua, Guyana and Belize in Concacaf qualifiers

In 2018, Iceland became the least populous country to compete in the FIFA World Cup™. If that achievement was improbable, then what Lee Bowyer is aiming to accomplish with Montserrat is almost inconceivable.

The Caribbean island is home to less than 5,000 people – Iceland’s population was around 330,000 in 2018 – but Bowyer is out to defy conventional wisdom and write one of the most astonishing stories in World Cup history.

“I like a challenge, and this is definitely a challenge,” says Bowyer. “It’s one I’m up for. Our ambition is to qualify for the World Cup and we’ll leave no stone unturned. We’ve got some good players and anything is possible.”

Having been appointed in September 2023, two-and-a-half hours on the training pitch was all Bowyer had before his first match in the dugout against Barbados. He immediately got to work on implementing a possession-based new style and formation. His methods paid dividends, with captain Lyle Taylor – who played under Bowyer at Charlton Athletic and Birmingham City – scoring a dramatic late winner in a 3-2 victory.

Like the majority of Bowyer’s squad, Taylor grew up and resides in England and has Montserratian heritage. The island nation is a British Overseas Territory and has long-standing immigration links with the United Kingdom. Indeed, when a volcano eruption in the mid-1990s rendered swathes of Montserrat inhabitable, much of the population moved to the UK.

“I’ve quickly found out the players are very passionate about playing for their country,” says Bowyer. “Whenever they step on to the pitch, they'll give everything they've got. While we may lack some quality in certain areas, we have big hearts.”

In his short time as Montserrat coach, currently 176th in the FIFA/Coca-Cola World Ranking, Bowyer has tapped into that deep national pride.

“I asked Lyle if the players get the honorary caps when they play a game, but they’d never seen anything like that before,” explains the former England international midfielder. “I spoke to the Montserrat FA president about getting the players caps and paying for them out of my own pocket.

“At the last camp, we gave the players their caps and some of them were in tears. They were so thankful, which made me smile. Some have kids and they'll have grandkids, so to be able show them that cap and that they've played for their country is huge.”

Bowyer has been welcomed warmly by the Montserratian people and describes them as “laid-back, friendly and always willing to help”.

“I actually got ill the last time I came here, my temperature went through the roof and I had to go to hospital,” he says. “The medical people couldn’t do enough for me, saying, 'Oh stay here for another 24 hours to make sure you're okay'. They were so attentive.

“Montserrat is a beautiful place. Even from our stadium, you can see the mountains and the sea. The island’s so small but it's stunning. I haven’t been able to take my wife yet, it’s hard with the kids at school, but she’s very keen to come!"

Bowyer still lives in England and regularly watches his UK-based Montserrat players in action. Some are contracted to likes of Reading, Barnsley and Fleetwood Town, while others are part-time and play non-league football. A key priority for Bowyer is identifying talent eligible to represent Montserrat and selling them the country’s World Cup dream.

“My pitch is: come and be part of something,” he says. “There is a lot of ambition here and we're trying to achieve something big, to qualify for the World Cup. Be part of the journey and, along the way, you'll improve as a player. I'm arranging meetings with a couple more young players who are eligible for us, and also meeting their parents. I think that's important. They must feel comfortable with their lads going away and playing for us.”

It is easy to imagine Bowyer putting forth a compelling case for joining his squad. His responses throughout our 45-minute interview are considered, expansive and delivered with clarity and conviction.

“Honesty, I believe, is the biggest thing in football,” he says. “That was the first thing I told the players, that I’ll always be honest with them. And if you want to ask me a question, please be prepared to be told the truth. Because that's all I ever wanted as a player.”

Now 47 years old, Bowyer boasts two decades of experience in the professional game. A tigerish and technically gifted midfielder, he made 397 Premier League appearances – scoring 57 goals – for the likes of Leeds United, West Ham United, Newcastle United and Birmingham.

Bowyer played under several revered coaches and outlined the influence they’ve had on his philosophy.

“I’ve taken bits from all of them – and you learn from both the good and bad things,” he says. “With George Graham [at Leeds], you had to work hard. That was it. If you didn't, you didn't play.

“Then you have someone like Sir Bobby Robson at Newcastle, whose man-management skills were unbelievable. That’s huge, especially in today's game, because you need to make players feel important and wanted. Sir Bobby had a way of dropping you, but still making you feel special. You'd come out of a meeting thinking, ‘I'm not happy I've been dropped, but I'm walking out with a smile on my face because of the way he’s done it!’”

Bowyer’s managerial career started at Charlton and he oversaw the club’s League 1 promotion campaign in 2018/19. His next job was at Birmingham City, who he guided to Championship safety after taking over when they were in a precarious position late in the 2020/21 campaign. Bowyer departed the club following a challenging second season and, after a year away from coaching, has been reinvigorated by his new role with Montserrat.

Back-to-back victories in their latest international camp – including a 2-1 win over Dominican Republic, which has population of more than 11 million – mean spirits are high ahead of their next get-together in March.

The real crunch action follows in June, however, when Montserrat kick off their bid to reach World Cup 26. The group-phase draw for the Concacaf qualifiers was made on Thursday, with Bowyer's side pitted against Panama, Nicaragua, Guyana and Belize.

“It's going to be tough to qualify, I know that,” says Bowyer. “I'm a realist but you never know. I’ve only been in charge for six games and I’ve already seen a big improvement in the players. We might need some luck, but football's crazy and it can throw up the odd mad moment. I'm a very positive person and my glass is always half-full.”

Twenty-two years ago, Montserrat contested ‘The Other Final’ – a match between the two lowest teams in the FIFA World Ranking. They lost to Bhutan on that occasion, with the game taking place on the same day Germany and Brazil faced off in the 2002 World Cup final.

If that was a low point for Montserrat, Bowyer is intent on building on the early promise of his tenure and laying the foundations for sustained success.

“I’ve signed a three-year contract and I want to build something here,” he adds. “We’ve got a strong group of players now, but I want to make sure there’s youth coming through and Montserrat is in a good place whenever I go, whether that’s in three or ten years.

“Yes, we want to qualify for the World Cup, but it’s about more than that. We need to build a future for Montserrat.”