It promises to be an entertaining day of tennis on day four at the ATP Shanghai Masters with 18 matches on the slate and, as always, we here at LWOT will be offering our predictions for every match on the slate, including Jannik Sinner vs Taro Daniel, Mattia Bellucci vs Alexander Zverev, Lorenzo Musetti vs David Goffin and Carlos Alcaraz vs Shang Juncheng. But who will advance?

ATP Shanghai Day 4 Predictions

Jordan Thompson vs Tallon Griekspoor

Head-to-head: Thompson 1-1 Griekspoor

Jordan Thompson  will be disappointed with his results at the just concluded ATP Tokyo after starting off his campaign brilliantly. He defeated Casper Ruud in straight sets in the first round but missed out on a quarterfinal berth in the ATP 500-level event after failing to replicate his first round performance against Kei Nishikori in the second round.

This is an immediate opportunity for the Aussie to make amends for last week’s disappointment, as he failed in the first round at the Shanghai Masters in 2023. In fact, both of his previous main-draw matches at this venue ended in losses, against Diego Schwartzman in 2017 and Terence Atmane in 2023.

In contrast, Tallon Griekspoor lost his top-30 status and is heading toward the top 50, reflecting his underwhelming performance and results over these nine months.

He is not finding ways to win any easy matches these days, and even at the Shanghai Masters this week, he needed three sets to overcome the clay-courter Facundo Diaz Acosta. Nevertheless, it was a positive outcome as it ended his four-match losing streak in Masters tournaments and also took his season win/loss record into the positive zone.

It is difficult to pick between these two players right now but all indications point to Thompson being best positioned to take advantage in this match.

Prediction: Thompson in 3
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Grigor Dimitrov vs Zizou Bergs

Head-to-head: Dimitrov 1-0 Bergs

Grigor Dimitrov remains one of the players vying for a spot at the ATP Finals, a tournament he won in his only previous appearance in 2017. However, his pursuit of that goal hit a snag of late. He made an impressive return to the top 10 recently but has faced a setback since Wimbledon due to injury. This issue continues to affect him, as reflected in his recent inconsistent performances and results.

Following his retirement at Wimbledon, his preparation for the US Open was poor, and he was again forced to retire at the season’s final Grand Slam in New York. Since then, he has played only one match, facing an out-of-form Alejandro Tabilo at the Laver Cup. His performance in that match was unconvincing, as he came close to being pushed to a deciding set.

A strong result at the upcoming Shanghai Masters would give him crucial momentum heading into the European indoor swing and reignite his quest for ATP Finals qualification. Though he struggled at this venue early in his career, his last two appearances were memorable—reaching the quarterfinals in 2017 and the semifinals in 2023, defeating Carlos Alcaraz in the round of 16.

Zizou Bergs defeated local favorite and last month’s ATP Hangzhou runner-up, Zhizhen Zhang, in straight sets during the first round of the Shanghai Masters. This marked Bergs’ debut at the tournament and his first-ever victory in the Asian swing. On Saturday, he will make his first appearance in the second round of a Masters tournament.

This has been a highly progressive season for the Belgian, not due to standout results, but because of his newfound consistency in playing closer to his potential and staying clear of major fitness issues. His performance has been strong over the past nine months, especially against top-20 players. Although he holds a 0-7 record in those matchups, he impressively took a set off them on five occasions and even led Rafael Nadal by a set at the Rome Masters.

Grigor Dimitrov leads the head-to-head 1-0 (four-set win at the 2024 French Open). Zizou Bergs has the quality and potential to trouble Dimitrov if the Bulgarian is still not in his best form or optimal fitness but the world no. 10 should have more than enough to come through.

Prediction: Dimitrov in 3
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Novak Djokovic vs Alex Michelsen

Head-to-head: first meeting

Novak Djokovic makes a welcome appearance at the ATP Shanghai Masters after a five-year hiatus. He has had an uncharacteristically underwhelming season according to the superhuman standards he has managed to set throughout his career – failing to win a single Slam – but there’s still a lot to play for in these last few months and the Serbian will no doubt remain one of the favorites here at a tournament where he holds the record for the most titles.

Alex Michelsen for his part got through a tricky test in the first round against local hopeful Bu Yungchaokete. The young American will no doubt relish the prospect of playing against the greatest of all time and should be able to hang with the Serb for a few games but Novak’s record at this venue should more than compensate for his lack of playing time the last few weeks and would get him across the finish line.

Prediction: Djokovic in 2

Main photo credit: Amber Searls-USA TODAY Sports