The Masters GOAT meets the Masters giant killer in Saturday's tantalising Shanghai semi-final, as Novak Djokovic squares up to Valentin Vacherot for a place in the showpiece event.
The Serbian superstar took down Zizou Bergs in the last eight to add yet another record to his collection, while his Monegasque foe added Holger Rune to his list of extraordinary upsets.
Match preview
Grand Slam number 25 went begging for Djokovic in 2025, and the 24-time major winner has also failed to conquer any of the earlier ATP 1000 events in the calendar year, prolonging his run for another Masters crown.
Not since Paris 2023 has Djokovic conquered a competition at this level, but with Carlos Alcaraz withdrawing, Jannik Sinner retiring and Alexander Zverev suffering a surprise third-round exit, the 38-year-old is the top dog remaining in Shanghai.
The 40-time ATP 1000 champion slogged it out in gruelling three-setters with Yannick Hanfmann and Jaume Munar to progress to the final eight, where he reverted to type with a 6-3 7-5 victory against Belgium's Bergs, thus becoming the oldest male singles semi-finalist in Masters history.
Sweltering heat and lower-body physical problems proved no match for Djokovic, who produced a quintessential dogged defensive display with just eight unforced errors and four out of five break points saved against the bedazzled Belgian.
As the pair were about to shake hands at the net, Bergs exclaimed "I need to stop idolising you!" to his conqueror, who is potentially just four sets away from a fifth Shanghai Masters crown from six finals; last year's loss to Sinner is the only aberration on his record.
Then again, Djokovic has more Shanghai semi-final defeats on his record (five) than he does titles at the ATP 1000 event, and the Serbian powerhouse will take nothing for granted against his Monegasque foe on a magical journey.
Sitting just outside the world's top 200, 26-year-old Vacherot had to navigate his way through qualifying just to earn a ticket to the main draw, but the Monaco trailblazer has since been stunning revered names left, right and centre.
Laslo Djere, Alexander Bublik, Tomas Machac (who retired at 0-6 1-3 down) and Tallon Griekspoor all fell to Vacherot's venom before the world number 204's quarter-final date with Denmark's Holger Rune, who became the latest victim of the record-breaking underdog.
Vacherot's astounding 2-6 7-6[4] 6-4 victory saw Vacherot become the lowest-ranked ATP 1000 semi-finalist since the turn of the millennium, and the first player from Monaco to ever reach the last four of a men's singles Masters event; no wonder he broke down collapsed on the court as soon as Rune netted a forehand on match point.
Should the 26-year-old add the biggest scalp of all to his Shanghai record, a final fight with Daniil Medvedev, Arthur Rinderknech, Alex de Minaur or Felix Auger-Aliassime will await, although that is a very big if against arguably the greatest player to ever grace the court.
Tournament so far
Novak Djokovic:
First round: Bye
Second round: vs. Marin Cilic 7-6[2] 6-4
Third round: vs. Yannick Hanfmann 4-6 7-5 6-3
Round of 16: vs. Jaume Munar 6-3 5-7 6-2
Quarter-final: vs. Zizou Bergs 6-3 7-5
Valentin Vacherot:
First round: vs. Laslo Djere 6-3 6-4
Second round: vs. Alexander Bublik 6-3 3-6 4-6
Third round: vs. Tomas Machac 6-0 3-1 ret.
Round of 16: vs. Tallon Griekspoor 4-6 7-6[1] 6-4
Quarter-final: vs. Holger Rune 2-6 7-6[4] 6-4
Head To Head
Djokovic and Vacherot will be clashing at the top level for the very first time in Saturday's semi-final, and there are just the 100 ATP Tour titles between them - all of which belong to the Serbian.
The intriguing encounter pits right-hander against right-hander, although the Monegasque man has the slightest of physical advantages, standing at 6'4 compared to Djokovic's 6'2.
We say: Djokovic to win in two sets
If Saturday's showdown goes the distance, the man 12 years Djokovic's junior cannot be discounted, especially given the latter's leg and foot issues over the past few days in Shanghai.
However, Vacherot is yet to test his mettle against the Serbian's exceptional defence, and for all the underdog's giant killings this week, taking down Djokovic may be a step too far.