After 10 days of battling excruciating heat, breakout stories, and record-setting matches, the 2025 Shanghai Masters has finally welcomed its semifinal lineup. It’s an interesting one to say the least: two former champions vs two rising underdogs. Another slice of the 2025 tale, though, awaits to be stamped during the crowning moment; regardless of who gets to savor it.

In case you missed it, at the Madrid Open in May, Casper Rudd set a mark. At 26 years and 4 months old, he became the oldest player to clinch a major title (Grand Slam or Masters 1000) in  2025 up to that point. Now, here’s the thing: the youngest of Shanghai’s semifinalists, Valentin Vacherot, is already 26 years and 10 months old. So what does that mean?

With the Monegasque sensation already six months older than the previous record holder, whoever wins the title will officially become the oldest “big title” winner of the 2025 season. Here’s how the rest of the semifinalists lineup: Novak Djokovic (38), Daniil Medvedev (29), and Arthur Rinderknech (30). But truly, October 11th is the day set for real excitement with multiple records and storylines awaiting to be written.

Vacherot, who defeated No.11 Holger Rune 2-6, 7-6(4), 6-4 to storm into the semifinals, is set to face Djokovic in the first match of Saturday. The 26-year-old, who entered as World No. 204, became the second-lowest-ranked semifinalist in Masters 1000 history since the series began in 1990. The only player ranked lower to achieve that feat was American Chris Woodruff, who made the Indian Wells semifinals in 1999 while sitting at No. 550 in the world.

Vacherot built his run on resilience throughout the tournament, surviving two rounds of qualifying and grinding out comeback wins in nearly every match. And along the way, he took down No. 14 Alexander Bublik and No. 27 Tallon Griekspoor, improving to 6-1 against Top 50 opponents this season. His heroics have landed him as the new No.92, marking his first top 100; the only time he came close was in June 2024, when he reached 110 before a shoulder injury took him out. Djokovic, on the other hand, has been etching his own kind of history.

In defeating Zizou Bergs 6-3 7-5, the 24x Grand Slam champion extended his own record of becoming the oldest player to reach the last four of a Masters 1000 tournament – it marked his 80th trip to the semifinals. He also holds the record for most titles (40), finals (60) in Masters 1000, and looks poised enough to extend each of them. His competition, though, could further come in the form of Medvedev.

The Russian secured his 50th Top 10 win in defeating seventh seed Alex de Minaur 6-4, 7-5 during the quarterfinals match. To add to it, he has previously triumphed in Shanghai in 2019 and is on a quest to clinch his title no. 21. His first hurdle will be Rinderknech on Saturday.

The French man defeated 12th seed Felix Auger-Aliassime 6-3, 6-4 for his first-ever ATP Masters 1000 semifinal berth. If he happens to defeat Medvedev, Rinderknech could face his cousin, Vacherot in the finals. They say the family group chat is already buzzing.

So far, Roger Federer has managed to hang on to the ‘oldest Masters 1000 champion’ which he secured at the Miami Open in 2019, aged 37 years, 235 days. If Djokovic manages to go all the way through, the record will finally be rewritten. If the underdogs make it past, that’s a tale for all the qualifiers to hear about.