Wimbledon 2025, Day 8 Highlights: Legends in the Box, Drama on the Court

Writer-editor Harsh Pareek brings you all the courtside drama, flair and finesse from Wimbledon 2025, in #ServeAndVolley.

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WITH THE GRASS AROUND THE BASELINES wearing off and the All England Club putting out fires around their decision to replace the line judges with a (much contested) AI line-calling system — something that came into sharp focus on Sunday during a fourth round match between Anastasia Pavlyuchenkova and Sonay Kartal after it was turned off in error — we entered the second week of the Grand Slam. One steeped in history, but (ready) to embrace the future, as the Rolex ad keeps reminding us.

An overcast day gave way to quiet sunshine, and in the house were Roger Federer and wife Mirka to watch over the proceedings from the Royal Box. The splendid atmosphere would later make way for some shocking scenes on the Centre Court, but that was still some hours away.

First up, it was Croatian Marin Čilić against Italian Flavio Cobolli on Court 2. 36-year-old Čilić, who on his way here had seen off fourth seed Brit Jack Draper in the second round but had more gruelling encounters to contend with, seemed not at his best as he lost the first two sets 6-4, 6-4. By the time he got back into his rhythm an hour or so in, it was too late. The bristling 23-year-old, part of the Italian posse making waves at the tournament, clinched the match 6-4, 6-4, 6-7(4), 7-6(3).

On the women's side next, Switzerland's Belinda Bencic reached her first Wimbledon quarter-final in nine attempts after beating 18th-seeded Russian Ekaterina Alexandrova 7-6(4) 6-4. Serving for the second set and 5-3 up, Bencic had a bit of a meltdown as she continuously failed to close the match, with her team at the receiving end of her growing frustration. But the Tokyo 2020 Olympic champion held her nerve and will now meet another Russian, Mirra Andreeva, in the quarters.

Seventh seed Andreeva saw off American Emma Navarro with ease to become the youngest player to reach the last eight of the women's singles in the past 18 years. The one-sided affair where Navarro never found her footing ended 6-2, 6-3. On her Centre Court debut, 18-year-old Andreeva lost track of the score and was ready to go again before realising the job was done. With Federer watching over from the box, it was the post-match interview that proved to be a real highlight. “I really tried my best not to look over there. I knew as soon I would look there, I would completely lose my focus. So I did, at 4-1,” she told the crowd. “Honestly it means a lot to me that you came and watched my match. It’s been one of my dreams to see you in real life.” After complimenting Mirka's outfit, Andreeva moved to her coach, the Spanish Hall of Famer Conchita Martínez, who will be taking to the court for the legends doubles and swapping roles with the Russian. “I’m going to get my revenge, finally,” said Andreeva, who hoped to continue her dream run in the tournament.

Back with the men's, and it was a fast and furious one on Court 1 with 10th-seeded American Ben Shelton taking on the Italian Lorenzo Sonego. Shelton, who's had a relatively comfortable tournament so far, went a set down to Sonego, who had to carve out victories in the last couple of rounds. The American quickly hit back though, winning the second 6-1, and then digging in for a pulsating two sets, coming out on top 3-6, 6-1, 7-6 (1), 7-5. Not only had he now made it to the quarter-finals for the first time, in the process, one-upped his father and current coach Bryan who himself made it to the last 16 of Wimbledon 31 years ago, but never any further.

Meanwhile, Novak Djokovic, who has been sailing smoothly so far in his hunt for the 25th Grand Slam, found himself in some choppy waters as he lost his first set against 11th-seeded Australian Alex de Minaur 6-1 in 31 minutes. The seven-time Wimbledon champion was quick to recover, making de Minaur run around the court for his life, but had his share of uncomfortable moments. At one point in the fourth, the Aussie was 4-1 ahead, with a point for a 5-1 lead. But the Serbian closed the proceedings just in time for a final score of 1-6, 6-4, 6-4, 6-4. Federer once again was in the Royal Box for the match, this time watching over his former opponent. “It’s probably the first time he’s watched me and I won the match. The last couple I lost,” Djokovic said in the post-match interview. “So, good to break the curse.”

Speaking of breaking curses, Iga Świątek seems to be enjoying her time on the grass court. The eighth-seeded Polish took on the Danish Clara Tauson (in a retro cool-kid kit) on Court 1 towards the end of the day. The former world number one had a shaky start, with two double faults and dropping her serve to love, but managed to steady herself by immediately breaking back, but still taking some time to get on top after going 3-1 down. But from there on, a clearly out-of-sorts Tauson had little to give back, with the tie concluding 6-4, 6-1. Świątek will meet Russia's Liudmila Samsonova in the quarters, who herself beat Spain's Jessica Bouzas Maneiro 7-5, 7-5 on Court 2 earlier in the day.

Finally, it was time for top seed Jannik Sinner to take on 19th-seeded Bulgarian Grigor Dimitrov at the Centre Court. Sinner had blazed past opponents so far in the tournament, was the overwhelming favourite for the match, and had even put out a rather relaxed vlog on his YouTube channel just hours before that saw him practising and cooking on his day off. An equally carefree on-court Dimitrov, though, had other plans.

Sinner, who has not lost a set or even dropped a game so far, was 6-3 down before he could even get his bearings. Hampered by a right elbow issue after slipping and falling to the turf early on, the world number one called for a physio and tried to get back in it, but found himself a second set down. Amidst all this, to the annoyance of many, including Sir Andy Murray, the play had to be halted for the roof to be closed. But Dimitrov was having the game of his life, controlling the match, a packed crowd behind him for an upset.

Out of the blue, with 2-2 in the third, the Bulgarian hit an ace and then fell to the ground clutching his pectoral muscle. As a concerned Sinner walked around to check on him, the Centre Court was stunned into silence. A clearly distressed Dimitrov asked for a brief medical timeout, off the court, against all hope. He returned, face red and in tears, before shaking Sinner’s hand. This would be the 34-year-old's fifth retirement from as many Grand Slams due to various injuries. Sinner had dodged a bullet.

“I don’t take this as a win at all, this is just an unfortunate moment for us to witness,” the Italian said in a brief post-match interview. “If there was a chance for him to be in the next round, he would deserve it. I hope he has a speedy recovery.” Sinner will have much to think about, not to mention his bruised elbow, as he prepares to meet high-flying Shelton in the next round.

Matches to watch today:

Aryna Sabalenka vs Laura Siegemund

Amanda Anisimova vs Anastasia Pavlyuchenkova

Taylor Fritz vs Karen Khachanov

Cameron Norrie vs Carlos Alcaraz