Preview: Wimbledon: Jannik Sinner vs. Ben Shelton - prediction, head-to-head, tournament so far

Jannik Sinner survived a major upset on Centre Court on Monday as Grigor Dimitrov’s injury misfortune allowed the world No. 1 to reach another Wimbledon quarter-final, where he faces Ben Shelton in their seventh meeting on the ATP Tour.

The top seed, who sustained an elbow injury early in the match, was on the ropes after losing the first two sets, only for the Bulgarian to sustain a pectoral injury, forcing the 34-year-old to retire for the fifth consecutive Grand Slam, thereby meaning an ailing Sinner will take on 10th seed Shelton on Wednesday for a place in the semi-finals.

Match preview

There were heartbreaking scenes on Centre Court on Monday as Dimitrov suffered a pectoral injury that forced him to retire despite leading the No. 1 seed by two sets against in their last-16 contest.

Sinner entered Monday’s match having dropped just 17 games in wins over Luca Nardi, Aleksandar Vukic and Pedro Martinez, and was expected to secure another comfortable victory over his Bulgarian opponent, whom he had defeated in four consecutive encounters.

However, the Italian star could not cope with Dimitrov’s seasoned slices and attacking variety, which saw the experienced player deservedly win the opening two sets 6-3, 7-5, leaving the world No. 1 on the brink of a potential fourth-round exit.

While the 34-year-old’s injury misfortune benefits Sinner, the top seed is also far from fully fit heading into Wednesday’s quarter-final against Shelton, after injuring his elbow following a fall in the first game of the opening set against Dimitrov.

As of writing, the involvement of the No. 1 player in the match against the American remains uncertain — an MRI is scheduled for Tuesday — meaning the 23-year-old’s chances of reaching his second semi-final at SW19 are still in the balance.

After losing five consecutive matches against Sinner on tour, Shelton will be optimistic about reversing that trend against the top player.

While the 10th seed lacks Dimitrov’s attacking variety, his powerful serve and solid forehand will need to be at their best to trouble the world No. 1, who appeared physically vulnerable in the last 16.

Shelton, whose third consecutive Grand Slam victory over Lorenzo Sonego secured his spot in a maiden Wimbledon quarter-final, aims to reach a third semi-final at this level by upsetting the top-ranked player on the ATP Tour.

Having exited in the second round in his 2023 debut, the 22-year-old has now advanced to the last eight in his third main-draw appearance, improving on last year's fourth-round exit and emulating Andy Roddick's 2004 achievement as the youngest American to reach the quarters at SW19.

After failing to win a set against the 19-time titlist in five straight matches, Shelton, now 8-2 at Wimbledon, hopes to capitalise on the top seed's shaken confidence after his Dimitrov scare and an injured elbow to progress at the expense of the 23-year-old.

Tournament so far

Jannik Sinner:

First round: vs. Luca Nardi 6-4 6-3 6-0

Second round: vs. Aleksandar Vukic 6-1 6-1 6-3

Third round: vs. Pedro Martinez 6-1 6-3 6-1

Fourth round: vs. Grigor Dimitrov 3-6 5-7 2-2 ret.

Ben Shelton:

First round: vs. Alex Bolt 6-4 7-6(1) 7-6(4)

Second round: vs. Rinky Hijikata 6-2 7-5 6-4

Third round: vs. Marton Fucsovics 6-3 7-6(4) 6-2

Fourth round: vs. Lorenzo Sonego 3-6 6-1 7-6(1) 7-5

Head To Head

Australian Open (2025) – Semi-final: Sinner 7-6(2) 6-2 6-2

Shanghai Masters (2024) - Round of 16: Sinner 6-4 7-6(1)

Wimbledon (2024) – Fourth round: Sinner 6-2 6-4 7-6(9)

Indian Wells (2024) - Round of 16: Sinner 7-6(4) 6-1

Vienna (2023) - Round of 32: Sinner 7-6(2) 7-5

Shanghai Masters (2023) - Round of 16: Shelton 2-6 6-3 7-6(5)

Since beating Sinner in Shanghai two years ago, Shelton has suffered five straight losses to the Italian, failing to win a set in each encounter.

Nonetheless, both men have played out tiebreaks in their previous meetings, all favouring the top seed.

Wednesday’s match will be their third at a Grand Slam and second at the Championships in consecutive years, with all previous encounters going Sinner’s way, the most recent at this year’s Australian Open.

The American, now ranked in the top 10, has never beaten a top-10 player at a Grand Slam, and his overall record of 5-16 against elite players reflects his broader struggles against the game’s best.

We say: Sinner to win in four sets

A previously invincible Sinner appeared vulnerable against Dimitrov’s aggressive tennis and an injured elbow, putting his ambition to reach a second Wimbledon semi-final at risk.

Facing a player with fewer weapons than Dimitrov, the outcome on Wednesday likely depends on the top seed’s health and ability to return serve effectively against Shelton’s powerful deliveries.

If healthy enough to play, the top seed is expected to beat the 10th seed in four close sets, setting up a semi-final against either Flavio Cobolli or Novak Djokovic.

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