When asked about the ‘Italian generation’ – and the rise of Jannik Sinner – 27-year-old Matteo Berrettini took a moment to pay tribute to his compatriots, before striking a more contemplative figure.

‘Sometimes I think I was kind of like the first one of this generation, you know? Like I used to be the young one, and now I’m the older one.’

In June Sinner was inaugurated as the first Italian world No1 in the history of the sport’s rankings to great national fanfare, and is very much the face of his country’s tennis revolution.

Lorenzo Musetti, Jasmine Paolini, Elisabetta Cocciaretto and Matteo Arnaldi are among the talents flying the tricolore within the top 50 ranked players on the men’s and women’s tour, but few can touch the 22-year-old’s white heat, which sees Grand Slam trophies collide with sumptuous, composed form – and requisite lucrative sponsorship deals.

But just three years earlier, it was another Italian – early 20s, equally marketable, star firmly on the rise – that was making history, at Wimbledon, on Centre Court.

Matteo Berrettini is dangerously unseeded in the Wimbledon draw as he seeks to recapture his grass court supremacy

Matteo Berrettini is dangerously unseeded in the Wimbledon draw as he seeks to recapture his grass court supremacy 

But the 27-year-old will encounter a formidable opponent in his fellow Italian Jannik Sinner

But the 27-year-old will encounter a formidable opponent in his fellow Italian Jannik Sinner

After struggling with injury, Berrettini has made more headlines off the court than on it (pictured with ex-girlfriend Melissa Satta in 2023)

After struggling with injury, Berrettini has made more headlines off the court than on it (pictured with ex-girlfriend Melissa Satta in 2023)

The same weekend as an even greater Italian triumph 13 miles up the road at Wembley, Berretini stepped on court to face off with the mighty Novak Djokovic and become the first of his countrymen to feature in a Wimbledon final.

Berrettini was no tourist. He pushed Djokovic, scrapping for his 20th Grand Slam title, to four sets after bloodying his nose in the first via tiebreaker, and acquitted himself well.

The fortnight had been his – Berrettini had only been broken five times before stepping onto SW19 showpiece court, and served up over a century of aces in the highest haul of the tournament. Defeat to one of the all-time greats may have stung, but Berrettini was hardly a man alone in losing to Djokovic. His maiden Grand Slam final should have been a stepping stone, if not to consistently challenging on all surfaces, constructing a significant grass court legacy.

The 27-year-old is a man for the turf. Of his eight career titles, four have come on the surface, on which the Italian’s monstrous serves thrive, offering winding pace. His second weapon, a scything forehand, cuts with equal precision in grass court season, and his backhand deficiencies are better concealed on the greenery by a tricksy slice.

Berrettini made history when he walked onto Centre Court for his 2021 final versus Novak Djokovic (pictured with Italy captain Giorgio Chiellini, right, and Italian president Sergio Mattarella)

Berrettini made history when he walked onto Centre Court for his 2021 final versus Novak Djokovic (pictured with Italy captain Giorgio Chiellini, right, and Italian president Sergio Mattarella)

The player's grass court dominance has seen him win back-to-back titles at Queen's Club - where he celebrated his 2022 win with a bowl of pasta

The player’s grass court dominance has seen him win back-to-back titles at Queen’s Club – where he celebrated his 2022 win with a bowl of pasta

Hopes of back-to-back Grand Slam runs was stymied by a 2021 US Open re-run with Djokovic

Hopes of back-to-back Grand Slam runs was stymied by a 2021 US Open re-run with Djokovic

In a stroke of bad fortune, Berrettini was stopped in the quarter-finals of the US Open a month and a half later by Big Bad Djokovic, unable to take his revenge on a his weakest surface (Berrettini also has a hankering for clay) but the mood was unstinting. Berrettini started 2022 with a career-high ranking of No6 in the world, with few complaints.

Not all bodies are created equal. Just ask the two 37-year-olds, both born in May of 1987, how they’re feeling. The differences between a distraught Andy Murray withdrawing from his final Wimbledon singles run and Djokovic, looking electric three weeks after only the second surgery of his career, are stark. Berrettini is one of those Murray-types, forced to play under the dark star of persistent injury and sliding-doors misfortune.

The first instance came in the spring of 2022, when the player was forced to withdraw from the Miami Open to undergo emergency surgery on a hand injury. Missing out on the clay swing was a hardship, but a necessity to prove fitness on grass, and upon his return, Berrettini won the titles at Stuttgart, and Queen’s Club in a pitch-perfect Wimbledon primer.

Instead, Berrettini was hit by an absurd curveball – a positive Covid-19 test – that mandated his withdrawal from the tournament. The impact of missing out on a swing at his favoured Slam was devastating.

Saying at the time that he was ‘heartbroken’, Berrettini later openly pondered whether if the universe was acting against him.

Berrettini has spent the last two years battling a litany of injuries, illnesses, and bad luck

Berrettini has spent the last two years battling a litany of injuries, illnesses, and bad luck

The player has been forced to retire on a number of occasions as he battles for full fitness

The player has been forced to retire on a number of occasions as he battles for full fitness

‘It was absurd,’ Berrettini said at the time. ‘At one point I clung to the hope that I had been positive before and I could be negative on Tuesday. But this did not happen.

‘At open point we said to ourselves there is something or someone who is cursing us.’

2023 would see things turn from bad to worse, as he was forced to withdraw from a match at Monte-Carlo with an abdominal injury, a later diagnosis of an oblique tear barring him from a run on clay, and his typical Wimbledon warm-ups.

Months later, at the US Open, it was an ankle injury which knocked him out for the remainder of the season, and saw his ranking – already up-and-down amid injury-riddled form – plummet.

‘I lost the joy for the sport,’ Berrettini said starkly in the thick of his cursed run of injuries. ‘I lost everything… that’s for me what makes me feel alive.’

The Italian also spoke that year of the ‘never-ending story’ he was experience, the feeling of being stuck on a loop of frequent injury.

‘I saw everything dark. I thought there was going to be no chance I was going to be able to play again. (I had) so many thoughts, negative thoughts’.

Off the court, Berrettini is sponsored by Hugo Boss, and frequently appears in their campaigns

Off the court, Berrettini is sponsored by Hugo Boss, and frequently appears in their campaigns

Like Sinner, Berrettini has also dated a fellow player - Australian-Croatian Ajla Tomljanovic

Like Sinner, Berrettini has also dated a fellow player – Australian-Croatian Ajla Tomljanovic

The pair were an item for three years, with the tail-end of their relationship captured on film

The pair were an item for three years, with the tail-end of their relationship captured on film

Berrettini and Sinner’s meeting on Centre Court, for all their shared nationality, will be a meeting of opposites. The younger man’s meteoric rise has seen far fewer impediments, at times appearing effortless, much like his cool, graceful playing style.

The 27-year-old acknowledged on Monday after beating first-round opponent Marton Fucsovics that ‘definitely, we are different personalities’. Sinner, all Italian sprezzatura, sponsored by Gucci, and in Berrettini’s words ‘so natural’. On the other side of the net, Berrettini appears rougher, a tattooed battler with more visible flaws in his game, and a more visible life away from the game.

Unlike Sinner, who only recently went public with his tennis player partner Anna Kalinskaya, Berrettini is an old hand at dating across the ATP-WTA divide, having been in a relationship with Ajla Tomljanovic between 2019 and 2022. Their partnership was initially tinged with reality-TV edge, due to the Australian player’s prior relationship with Nick Kyrgios.

Somewhat fittingly, the relationship soon found its home there, featuring as a major plot point on short-lived tennis docu-series Break Point, filmed sparring at the Australian Open just weeks before their February 2022 break-up.

For her part, Tomljanovic has said she has ‘no regrets’ about airing her private life to Netflix’s hungry audiences, and Berrettini joked that he had actually ‘liked that episode a lot’, suggesting the pair remained amicable years on from the breakdown of their relationship.

Berrettini then went public with TV presenter Melissa Satta - who is 10 years his senior

Berrettini then went public with TV presenter Melissa Satta – who is 10 years his senior

The former wife of Kevin-Prince Boateng in the past courted controversy for statements on her active relationship

The former wife of Kevin-Prince Boateng in the past courted controversy for statements on her active relationship

The model was branded a 'sex addict' by tabloids in Italy, but Satta responded to controversy in good humour

The model was branded a ‘sex addict’ by tabloids in Italy, but Satta responded to controversy in good humour

A year later, Berrettini went public with another famous partner, Italian model and television host Melissa Satta, who had previously dated ex-Italy international Christian Vieri and been married to AC Milan and Schalke star Kevin-Prince Boateng.

Satta picked up notoriety when in 2012, she tongue-in-cheek blamed Boateng’s own persistent injury problem on his overactive schedule away from the pitch, claiming that the pair ‘had sex seven to 10 times a week.’

The former showgirl added that she ‘hated’ foreplay and preferred to be ‘in control’ during their apparently strenuous couplings, but met with humourless commentary in the aftermath, told Gazzetta dello Sport: ‘You have to be very carefully what you say in football, especially when it comes to sex’. There have been no such admissions about Berrettini.

Dating Satta – paired with a string of high profile endorsements including Boss and Red Bull and faltering form – attracted ire from former French Open champion Nicola Pietrangeli, who said that he feared Berrettini ‘devoted himself more to advertising to tennis’ and derisively called him ‘very handsome from the waist up, but his legs don’t move as they should’.

Ahead of 2024, Berrettini began working with Francisco Roig (background), who previously worked with Rafael Nadal

Ahead of 2024, Berrettini began working with Francisco Roig (background), who previously worked with Rafael Nadal

The Italian will hope that he stays injury free in a bid to return to his previous dazzling form

The Italian will hope that he stays injury free in a bid to return to his previous dazzling form

The couple have since parted ways, with Berrettini playing tribute to their ‘beautiful and intense’ relationship, just months after the player split with his coach of 13 years, Vincenzo Santopadre.

Meeting Sinner on Centre Court will prove a tough ask, but Berrettini will be unencumbered by expectation. His injury woes have run into 2024, with the player battling a GP’s waiting list of gastrointestinal issues, a foot injury, tonsillitis, and a fever as the clock has counted down to Wimbledon. But little renews Berrettini’s spirit like returning to grass, and the court were he made history.

As does the prospect of facing off with his compatriot.

‘Personally, it gives me so much energy,’ Berrettini said in his final remarks before their meeting, ‘to just try to be there and to play against him, and to be at his level.

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