What happened to the 'Golden Boy' of tennis who was called the left-handed Roger Federer

Canadian tennis player Denis Shapovalov was once tipped by many to be the next Roger Federer due to his one-handed backhand, but the 26-year-old has yet to reach a single major final. So what happened to the once-hot prospect?

Shapovalov, who was born in Israel but represents Canada having moved there when he was one, was known for his explosive left hand, which helped him win the 2016 Wimbledon boys’ singles title.

“I love the guy, he reminds me of someone, someone who used to play this game long ago,” John McEnroe said of Shapovalov back in 2017.

“It’s awesome, he’s learning quickly, he believes in himself, it’s amazing to sort of watch yourself in the mirror.

“He plays the way I’d play if I was 18 now. The game has changed, but in essence he’s doing the same thing.”

Despite starting his professional career with an esteemed reputation, the Canadian quickly ran into controversy at the 2017 Davis Cup.

A then 17-year-old Shapovalov angrily hit the ball out of the court while facing Great Britain in Ottawa, only for it to strike umpire Arnaud Gabas in the eye.

Shapovalov rushed towards the umpire to check if he was okay, but this did not help him avoid a default.

He later issued an apology and branded his own behaviour “unacceptable”.

The teenager received a $7,000 fine for his actions.

Denis Shapovalov was once tipped for great things (Credit:Getty)

However, he helped rebuild his reputation later that year when he defeated Rafael Nadal, then world number one, at the Rogers Cup.

After his unlikely victory over the Spaniard, the Canadian said that his “dream” had come true, having watched the likes of Nadal and Federer from a young age.

Shapovalov went on to reach the semi-finals of the tournament before losing to Alexander Zverev, becoming the youngest ever Masters 1000 semi-finalist at 18.

In 2018, Shapovalov continued to impress by reaching the Madrid Open semi-finals before losing to Zverev again. His consistent performances saw him break into the ATP top 30 in May 2018.

The following year, he showed further glimpses of brilliance, winning his first ATP title at the Stockholm Open, defeating Filip Krajinović in the final. He also reached the Paris Masters final, where he lost 6–3, 6–4 to Novak Djokovic.

In 2020, he continued to progress, reaching a career-high ranking of world number 10 following a strong run at the US Open, where he reached the quarter-finals.

He arguably reached his peak in 2021 when he made the Wimbledon semi-finals, beating Andy Murray in the third round before losing to Djokovic. In the same year, he was part of the Canada team that won the Davis Cup. However, he withdrew from the Tokyo Olympics citing COVID-19 concerns.

Also in 2021, he pulled out of the French Open due to a shoulder injury.

In 2022, Shapovalov reached the quarter-finals of the Australian Open but struggled to progress beyond the early rounds of the other three majors.

The following year was expected to be crucial in his development, but his progress was halted when he missed around six months of the season due to a knee injury sustained at Wimbledon. As a result, his ranking dropped significantly before he returned in 2024.

“It’s been a real tough journey to come back,” Shapovalov told ATPTour.com. “It is never easy to come back from an injury, especially when you take six months off. You feel you need to catch a break. I think I started to play as soon as I could and maybe it was a little bit too early. I wasn’t completely ready tennis-wise, but you do need to play matches and tournaments.”

However, he struggled to find form upon his return, exiting several tournaments in the early stages. He went out in the third round at both the French Open and Wimbledon, and failed to get past round one at the US Open and Australian Open.

In 2025, his struggles continued, once again failing to get beyond the third round of any major. However, he did claim a title in Los Cabos, beating Aleksandar Kovacevic 6–4, 6–2 in the final.

In June 2025, he admitted he was still “trying to get back” to his pre-injury level.

So far in 2026, he has reached the second round of the Australian Open, but there are still no clear signs that the 26-year-old will replicate the Federer-like heights he was once tipped to reach.

Of course, at 26, there is still time for Shapovalov to win major titles. However, elite players such as Jannik Sinner and Carlos Alcaraz are unlikely to make that easy.