Jaspreet Singh inadvertently found himself in the middle of a historic moment. When he bowled the last ball of the men's T20 World Cup Europe qualifier, Netherlands' Max O'Dowd pulled it to deep midwicket to give his side a nine-wicket win, but it also sealed Italy's first-ever qualification for the 2026 men's T20 World Cup, alongside Netherlands.
Jaspreet moved to Italy from India in 2006 as a cricket-crazy teenager when his father brought the family over to Telgate, a town about 60km north-east of Milan. A few years later, Jaspreet was playing informal tape-ball games and eventually got into the Bergamo Cricket Club, about 40 minutes from his town. He started playing in matches organised by the Italian Cricket Federation (FCRI) from 2016-17, which paved the way to his international debut in 2019.
Crishan Kalugamage was 15 when he moved to Lucca, a town in central Italy, from Sri Lanka. He got into athletics for the first five to six years before playing amateur cricket in the local clubs from 2012. Three years later, he was spotted by a coach from Roma Cricket Club and went on to make his international debut in 2022.
The qualification of Italy - the only European team other than Netherlands to make it to the 20-team World Cup - comes at a time when the country's football is in shambles - the Azzurri didn't qualify for the FIFA World Cup in 2018 (for the first time since 1958) and 2022, and are in danger of missing the 2026 edition as well.
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Kevin O'Brien has already been part of some World Cup epics for Ireland as an allrounder. In 2022, he took up a different kind of challenge: he was asked to go over to Italy for a couple of days to review some local players and scout others for their national side. Instead, he ended up becoming Italy's assistant coach.
"It's absolutely amazing for me as a relatively new coach," O'Brien tells ESPNcricinfo. "I am still finding my feet in the coaching world, but I am glad to be able to help players achieve something that not many would have thought they would."
O'Brien found Italy to be in a similar situation to what Ireland were in in 2007, when he was part of the team that beat Pakistan and Bangladesh in the World Cup: plenty of enthusiasm, talented players, with belief that they could win matches, but lacking the facilities needed for professional sport.
"I think I can help the Federation navigate their way through this and identify what they need to improve at home, first and foremost, so that the players coming up in age-group cricket can train in better facilities in Rome or Milan or Bologna and better their skills."
The group of players O'Brien helped identify along with former captain and coach Gareth Berg have largely the same background of either having moved to the country or having familial roots there. Captain Joe Burns' grandfather was an Italian prisoner-of-war in North Africa, and his family emigrated to Australia after the Second World War. Ben and Harry Manenti's parents also relocated to Australia after the war for better opportunities. Emilio Gay, Thomas Draca and Grant Stewart's mothers are Italian while both parents of Anthony and Justin Mosca are from the country. For the likes of Gay, Stewart and the Manenti brothers, among others, playing for Italy doesn't hamper their chances of playing for England or Australia, should the opportunity arise.
Besides O'Brien, Italy also recruited support staff with prior World Cup experience - head coach John Davison, the former Canada captain, played the 2003, 2007 and 2011 World Cups, while assistant coach Dougie Brown played for Scotland at the 2007 World Cup.
Two weeks before the Europe qualifier started, the team gathered at the Italian National Olympic Committee (Comitato Olimpico Nazionale Italiano, CONI), the organisation that manages all sport in Italy. With cricket now being part of the Olympics, players are required to be regularly tested for fitness at CONI. After a few sessions there, they trained at the Roma Cricket Club on artificial turf, because Italy has no grass pitches, and then moved to Horsham, in West Sussex, to play three T20 matches against an Abu Dhabi T10 team. A couple of matches against Scotland and Guernsey in the Netherlands also helped lock in roles for every player and iron out any last wrinkles before the Europe qualifier.
Peter di Venuto, Italy's manager for the qualifier, has been part of the set-up since 2023 and a witness to the team's past fumbles.
"Two years ago [during the Europe Region Qualifier] in Scotland, we lost to Ireland by seven runs. Scotland also beat us by 155 runs in that competition," di Venuto, brother of Australia's batting coach, Michael, recalls. "If we'd beaten Ireland at that time, we would have been at last year's T20 World Cup."
This time though, Italy claimed a 12-run win over Scotland, which was key to sealing their World Cup spot. Gay scored a 21-ball 50 while Harry Maneti was the Player of the Match for his five-wicket haul and a run-a-ball 38. Before the qualifier, Italy had played a warm-up match against Scotland, which they lost by 40 runs, but it gave them a chance to put into practice things they wanted to do in the tournament proper. "It gave us good insight as to how they [Scotland] would play, how we expected to play, and then, when it came to the game itself, we were absolutely confident that we could win it," di Venuto says. "The fact that it became a reality is something the players will treasure forever. Sometimes the game has a way of rewarding those who believe and put the work in to achieve [something], and these guys have done that."
Di Venuto noted that not a lot had changed in Italian cricket in the last two decades, but with Italy hosting the Europe Sub-Regional Qualifier A last June, a couple of grounds were upgraded, which helped.
"[Qualification for the T20 World Cup] is a game-changer, it's a legacy that this team will leave for Italy cricket," di Venuto says. "The fact that Italy is starting to progress [will lead to] facilities [that] will help progress the game. With the additional funding that will come about due to rankings, due to the ten games of the World Cup, with additional sponsorship, there is a real opportunity for Italian cricket to be able to make a difference with regards to facilities. And that's exactly what the players are motivated for."
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Sixty-seven-year-old Simone Gambino is the founder of FCRI and has been part of cricket's journey in the country since the 1970s. He delves into the history of the game in Italy: "At the end of the 19th century, only expats played cricket in Italy, which was unified only in 1870. The British invested a lot of money in brokers and textiles and sent a load of people to work. These people put up combination 'soccer-cricket', which was playing soccer in the winter and cricket in the summer," Gambino says. "This still carries [on] in the names of two soccer clubs in Italy - AC Milan and Genoa, which are both carrying their names from cricket, although they no longer play it. "After World War I, Mussolini prohibited any English activity other than soccer, but post World War II, young catholic priests from India and Sri Lanka came into colleges and played cricket. This helped the game flourish in the 1960s, but cricket in Rome went down in the '70s."
As a teenager in the '60s, Gambino would travel to England to visit his grandfather, who taught him to play cricket and made him fall in love with the game. So when he saw cricket was declining in Italy, Gambino decided to take matters into his own hands.
"I thought the only way we can run cricket is to get the Italians involved and take it away from being an exclusively expatriate game. A period of 15 years followed in which cricket was played by indigenous Italians. The standard was very poor, but there was Italian cricket."
The FCRI was founded in 1980, and in 1995, the ICC granted Italy Associate status, which helped cricket regain some of its popularity in the country. For added impetus, or as Gambino calls it, "the biggest shock", Italy beat England in the European Championships in 1998. Though there weren't any frontline England players in the tournament, cricketers with first-class experience were involved. "[Former South Australia batter] Joe Scuderi scored a hundred and this game changed the scenario for us, because suddenly we were in the limelight," Gambino says.
Italy narrowly missed out qualifying for the 2003 men's World Cup after the ICC deemed four players in the squad - di Venuto and Scuderi among them - ineligible and Gambino withdrew the team from the 2001 ICC Trophy, which was the pathway for qualification for the World Cup. Italy were one of the favourites, but in their absence, Netherlands, Canada and Namibia went through. Currently, Italy are second in the CWC Challenge League Group B, from which the top two teams go to the Qualifier playoff for the 2027 ODI World Cup.
With a lot of players in the Italy squad being dual citizens, their training and upskilling happens elsewhere - Burns and the Manenti brothers play domestic cricket in Australia; Gay and Stewart play county cricket in the UK; Middle-order batter Wayne Madsen is Derbyshire's first-class captain. Jaspreet largely trains in Birmingham and plays in the Birmingham District Premier League.
Gambino knows that for the sport to get better in Italy, it is imperative that the supply chain at the grassroots is stronger. "I find it fascinating that you have this rule in India that every player can play the Under-19 World Cup only once," he says. "You will only grow by pushing forward. This is culturally difficult for us in Italy right now, because [although] so far the ICC has given us funds and helped us in building infrastructure, the only thing you cannot instill immediately is culture. That needs time, at least a generation, if not more.
"So this qualification means hoping to end the era of survival and taking one big step forward. There are two great means of expansion of cricket in any country in the world - one is the building of infrastructure and the second is entering schools. These are the steps we need to take using the World Cup as a silver trampoline, as a launching board."
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The players, who work five-six days a week, squeezing in time in between for practice and training, have had to make several sacrifices along the way to further their dreams of playing international cricket. Kalugamage had to quit his job as a pizza maker in a restaurant to train and play the Qualifier. Jaspreet had to give up driving an Uber in the UK. Others had to take longer breaks from their gigs as drivers or factory workers.
Despite the magnitude of what they have achieved, Kalugamage wasn't expecting a lot upon his return to Lucca. But he came back from the Hague, where the Qualifier was held, to find that more than a hundred people had turned up at his house, bringing him flowers and sweets. His phone buzzed non-stop with congratulatory messages. "I was very emotional, it was surreal," he says.
Jaspreet is cognisant of the significance of their achievement. "Even when we get old, we'll know that we were part of the first Italy side that qualified for a cricket World Cup and played. It is a big deal, a proud thing."