Only three men have pushed Novak Djokovic to a fifth set during the Serbian’s 33-match Wimbledon win streak: Rafael Nadal in the 2018 semi-finals, Roger Federer in the epic 2019 final and… Jannik Sinner in last year’s quarters.

While Djokovic never trailed in the set score on those occasions against his Big 3 rivals, he found himself two-sets-to-love down against Sinner last year on Centre Court before storming back for a five-set win. Can the Italian change the outcome on Friday if he finds himself in a similar position this year on the London lawns?

“First of all, you have to go up two sets to love,” he joked after beating Roman Safiullin to reach his first major semi-final.

“It’s going to be a completely different match than last year. He knows me better, as I know him better also. It’s going to be also a little bit tactical. In the other way, it is also a little bit mental. If you play against Novak, it’s always tough to play here, especially in Grand Slams.”

Prior to 2023, Sinner had reached the quarter-finals once at each major but never progressed beyond that stage. In three of those instances, he was beaten by the eventual champion.

Is the 21-year-old ready to become a major champion himself? Djokovic seems to think so.

“He’s playing on a very high level,” the Serbian said of his opponent. “He likes to play on grass. He likes to play on quick surfaces because he likes to be aggressive and take control of the point. From both forehand and backhand, he’s smashing the ball really, really hard, trying to be the one that is going to dictate the point from early on. I know his game well.

“He’s so young, so of course it’s expected that he’s going to improve. He is improving, no doubt, I think with the serve, he’s been serving better. On grass, it obviously makes a difference. He’s a very complete player.”

Unstoppable 🔥@DjokerNole takes out Andrey Rublev 4-6 6-1 6-4 6-3 to make it to his 46th Grand Slam semi-final 👊Wimbledon?ref_src=twsrc%5Etfw”>@Wimbledon pic.twitter.com/EqWqdy2lWs

— ATP Tour (@atptour) July 11, 2023

But for all the praise, the World No. 2 left no doubt that he expects to win. He fought off inspired efforts from Hubert Hurkacz and Andrey Rublev in the previous two rounds, going four sets in both victories. After beating Rublev, he spoke about how he relishes being the man to beat at Wimbledon, where he is seeking his fifth straight men’s singles title and a record-tying eighth overall.

Djokovic may be playing even better than he was last year in London, having entered the grass-court major halfway to a calendar-year Grand Slam this year. But Sinner has raised his game, too.

“For sure physically I have improved. I’m much stronger. I can stay on court for many hours without suffering,” he said, discussing the improvements in his game since his previous meeting with Djokovic 12 months ago.

“I think also game-wise or tennis-wise I feel better. If I have to play the slice, I can play it now without thinking. Before was always a little bit different. I can go to the net knowing that I have good volleys. I have some good things now in my game, and hopefully I can use it in the right way.”

Sinner called facing Djokovic at a Grand Slam tournament “for sure one of the toughest, if not the toughest, challenge”, but the Italian has plenty of big-match experience in his own corner. He is a seven-time tour-level champion and has reached two ATP Masters 1000 finals, both in Miami (2021, 2023).

A first major crown would see Sinner rise from his current career-high Pepperstone ATP Ranking of No. 8 to World No. 4 — though a runner-up finish would not change his standing. Djokovic, in addition to bidding for a record-extending 24th Grand Slam men’s singles title, is also seeking to reclaim the top spot in the Pepperstone ATP Rankings this week.

The Serbian could have that distinction secured by Friday night, should a win against Sinner be coupled with a semi-final defeat for World No. 1 Carlos Alcaraz against Daniil Medvedev. But if it is to be Djokovic vs. Alcaraz in Sunday’s final, the championship matchup would double as a straight shootout for No. 1.

Carlos Alcaraz and Daniil Medvedev face off for the second time at Wimbledon in Friday’s semi-finals. Few expect a similar outcome to the pair’s second-round clash from three years ago.

Medvedev breezed past a then-18-year-old Alcaraz for the loss of just seven games at SW19 in 2021, in the Spaniard’s first professional tournament on grass. Within 15 months of that heavy loss, Alcaraz had become the youngest No. 1 in the history of the Pepperstone ATP Rankings after his rapid development into one of the most exciting players on Tour.

“When he was 17, which was actually not long ago, he was much less mature and younger, which is normal,” said Medvedev on Wednesday when asked about his early memories of Alcaraz’s time on Tour. “He was missing [a lot of balls]. Everyone saw that he’s amazing, but everyone was wondering if he was going to find the way to miss less while producing the same power. And he did, quite fast. That’s what’s pretty amazing.”

THIS IS WHAT IT MEANS 🥹 👏⁰⁰Carlitos glides into his first Grand Slam Semi-Final on grass 🌱

D. Rune 7-6, 6-4, 6-4⁰⁰Wimbledon?ref_src=twsrc%5Etfw”>@wimbledon | Wimbledon?src=hash&ref_src=twsrc%5Etfw”>#Wimbledon pic.twitter.com/4eoMcgBhLe

— ATP Tour (@atptour) July 12, 2023

Medvedev would know a thing or two about not missing. The 27-year-old is renowned as one of the most consistent ballstrikers on Tour, with his ability to retrieve ball after ball from a deep position key to his own rise to World No. 1 in 2022. On Friday, his baseline wizardry, combined with his powerful serve, will be key for the third seed’s chances of reaching his fifth major championship match.

“He’s really a complete player,” said Alcaraz of Medvedev on Thursday. “I’m going to say, like I think [Andrey] Rublev said a few times, he’s an octopus. He catches every ball. It is amazing. He’s an amazing athlete… He does almost everything well.”

After his 2021 Wimbledon defeat to Medvedev, Alcaraz had to wait until March this year to level the pair’s Lexus ATP Head2Head series at 1-1. The Spaniard did so in style by dropping just five games in the BNP Paribas Open championship match in Indian Wells. Despite the one-sided nature of that encounter, Medvedev says the faster conditions on Wimbledon’s Centre Court will enable him to counter Alcaraz’s power more effectively.

“I think Indian Wells is not going to count a lot here. It was so slow in Indian Wells,” said the World No. 3. “It’s not going to be the same. At Wimbledon, the ball bounces lower. The serve is more important. There, I felt like I couldn’t get free points with the serve.”

Although their Indian Wells clash proved tough for Medvedev, he and Alcaraz have enjoyed similarly stellar seasons prior to forging out their personal-best Wimbledon showings this fortnight. Medvedev has now won a Tour-leading 46 matches on the year, with Alcaraz second on 45, while the pair also leads the field with five tour-level titles each in 2023. If either lifts the trophy at the All England Club, they would leapfrog Novak Djokovic to claim first place in the Pepperstone ATP Live Race To Turin.

Most Tour-level Wins In 2023

It is Alcaraz who has shone more brightly during the ongoing grass-court swing, however. The 20-year-old is 10-0 on the surface this year, a tally which includes his run to a maiden grass title at the ATP 500 at The Queen’s Club last month.

In contrast, Medvedev was 2-2 on grass heading into Wimbledon, but he dropped just one set in his opening four matches at SW19 before holding off an inspired Christopher Eubanks in five to reach his first Wimbledon semi-final. The 20-time tour-level titlist is relishing the prospect of testing his level against Alcaraz, who has dropped just two sets en route to the semi-finals himself.

“It’s interesting to play someone like Carlos,” said Medvedev. “He is an amazing, amazing player. What he continues to do is just unbelievable. He doesn’t stop. I don’t think he will, but I’ve played a lot of great players in my career. I managed to win many times. So I’m going to try to do my best. If I show my best, I’ll have my chances.”

With Djokovic also into the semi-finals, Alcaraz has the added motivation of playing to retain his No. 1 spot in the Pepperstone ATP Rankings. The Spaniard must at least match the seven-time champion’s result in London to keep top spot, meaning a championship-match clash between the two would be a straight one-on-one shootout for top spot. Despite that looming prospect, Alcaraz is unlikely to be distracted against Medvedev as he looks to avenge his Wimbledon defeat from three years ago.

“He’s playing great here on grass. He has had a great, great year as well,” said Alcaraz of Medvedev, who is just 275 points behind the second-placed Spaniard in the Pepperstone ATP Live Race To Turin. “I lost the first match we played here on grass. So I have to learn [from that], but I’m going to enjoy the semi-final.

“I think I’m playing great, I have a lot of confidence right now, so it’s going to be a really good match, I think. I’m going to enjoy it.”

Wesley Koolhof and Neal Skupski held their nerve to book a championship-match spot on Thursday at Wimbledon, where the top-seeded duo edged Rohan Bopanna and Matthew Ebden in a tense semi-final.

The top seeds prevailed 7-5, 6-4 on No. 1 Court after claiming a decisive break at the tailend of each set against their sixth-seeded opponents. They converted both break point chances they had —one in the 11th game of the opening set and the other in the ninth game of the second set — to reach their second major final as a team.

Koolhof and Skupski have won eight ATP Tour titles together since pairing at the start of 2022, but until this fortnight the closest they had come to a Grand Slam title was a final appearance at last season’s US Open. The pair has dropped just one set across their five matches this year at SW19, where Skupski is attempting to become the first Briton to lift the men’s doubles trophy since Jonathan Marray triumphed alongside Frederik Nielsen in 2012.

Marcel Granollers and Horacio Zeballos also delivered a clinical semi-final display to advance to the final. The 15th seeds converted all three break points they earned in their 6-4, 6-3 victory against Kevin Krawietz and Tim Puetz.

Granollers and Zeballos are now 10-1 as a team at Wimbledon, where they also reached the championship match in 2021. The Spanish-Argentine duo have continued their fine Grand Slam form with their final run in south-west London, having already reached the semi-finals this year at both the Australian Open and Roland Garros.

The battle for No. 1 in the Pepperstone ATP Rankings is heating up ahead of the Wimbledon semi-finals. Both Carlos Alcaraz and Novak Djokovic have a chance to leave London in top spot.

Alcaraz currently leads Djokovic by 80 points in the Pepperstone ATP Live Rankings. If both players lose in the last four of The Championships, the 20-year-old will remain No. 1.

Otherwise, whoever earns the better result at the grass-court major will earn World No. 1. Alcaraz and Djokovic could play a winner-takes-all championship blockbuster for the trophy and World No. 1.

Pepperstone ATP Live Rankings (as of 12 July)

Daniil Medvedev began the week with a chance to return to World No. 1 by the end of the fortnight, but needed early losses from Alcaraz and Djokovic. Since that did not happen, the 27-year-old is guaranteed to leave SW19 as World No. 3.

However, Medvedev can insert himself in the battle for ATP Year-End No. 1 presented by Pepperstone by lifting the trophy. Medvedev is trying to earn that accolade for the first time.

Medvedev can immediately claim the lead in the Pepperstone ATP Live Race To Turin. If Medvedev, Alcaraz or Djokovic triumph at The All England Club, the champion will depart in first place in the Live Race.

The fourth semi-finalist, Jannik Sinner, has the chance to make the biggest move in the Pepperstone ATP Live Rankings. Currently No. 8, the Italian will ascend to a career-high World No. 4 if he wins the title.

If Sinner claims his maiden major trophy to make that surge, he would become the joint-highest-ranked Italian in Pepperstone ATP Rankings history. Adriana Panatta reached World No. 4 in 1976.

Sinner also can put himself in prime position in the Live Race. Currently fifth, he can ascend to fourth by making his first major final. Sinner is trying to qualify for the Nitto ATP Finals for the first time after competing in the season finale as an alternate following Matteo Berrettini’s mid-tournament withdrawal in 2021.

“Because of Tomas, I started to play tennis.”

Jakub Mensik grew up watching Tomas Berdych light up the ATP Tour. The former World No. 4 would often practise in Mensik’s hometown, Prostejov, Czech Republic, where the 17-year-old had the chance to first meet Berdych in 2011.

“I was five and I was one of the hundreds of kids who played with him, one point in Prostejov,” Mensik told ATPTour.com. “It was kids day [at a Challenger event], and Tomas Berdych and Ivan Lendl came to be there with the kids and enjoy the time. 12 years ago, I was just a little kid watching him and watching his matches. I met him and took a photo with him. At that time, he didn’t know who I was, but now it’s a completely different situation.”

It is a ‘different situation’ now because Mensik is a fast-rising star on the ATP Challenger Tour, trying to follow in the footsteps of Berdych. In May, the teen won his first Challenger title on the clay courts of Prague. A month later, while competing at his home tournament in Prostejov, Mensik and Berdych played an exhibition match on kids day at the UniCredit Czech Open, the same event where they posed for a picture in 2011. 

“[Tomas] has not played for four years but in Prostejov, he’s the player of the club. He would practise there and played Challengers there, like the Czech Open,” Mensik said. “It was really fun, I really enjoyed it. Because of Tomas, I started to play tennis. Now I had the opportunity to play with him.”

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In just his sixth Challenger outing, Mensik edged Berdych by two months to become the youngest Czech Challenger champion in history (since 1978). Mensik joined elite company in Prague, becoming one of four 17-year-old Challenger titlists in the past five years: Jannik Sinner (2019), Carlos Alcaraz (2020), Shang Juncheng (2022).

Despite being able to count how many Challengers he has played on two hands, the World No. 217 in the Pepperstone ATP Rankings stated that he is learning quickly.

“When I started this year playing a couple Challengers, it’s a completely different level than playing Futures,” Mensik said. “I played a few Challengers in Thailand and then a few in Europe, I was like a new guy there. I knew I could play with those guys, but I didn’t have the experience. After a few tournaments, I really started to trust myself and play my best game.

“In Prague, that tournament I felt very special on court. From the start, I beat the top seed [Radu Albot] and after that match, I was like, ‘Let’s continue’. Match by match, I felt more comfortable on the court. Then in a few days I became a champion. I felt very special and it was a very good experience for me. After losing in first rounds and qualifying rounds, I think it was faster than I expected.”

The 2022 Australian Open boys’ singles finalist is aiming to continue his rapid rise with a goal of being at the Next Gen ATP Finals, an eight-player field that features the season’s best 21-and-under players. Mensik is currently 20th in the Pepperstone ATP Live Next Gen Race.

“Of course to be part of the Next Gen Finals would be really good. At the start of the season, I was losing matches and now the last few months, I’ve played well so I can see the ranking is moving,” Mensik said. “Let’s see what the next tournaments will bring but it will be very nice. It’s of course one of my goals. But the big goal is to be a part of the US Open. It would be my first Grand Slam. US Open would be really good and moving to the Top 200 would also be very good.”

In order to achieve those goals, Mensik is working hard on the ATP Challenger Tour. The teenager is in action at this week’s Concord Iasi Open, where he will aim for the highest-ranked win of his career when he meets top seed Bernabe Zapata Miralles in Friday’s quarter-final.

Sixth seeds Rohan Bopanna and Matthew Ebden rallied from a set down Wednesday to book their ticket to the Wimbledon semi-finals.

The Indian-Australian duo survived Dutchmen Tallon Griekspoor and Bart Stevens 6-7(3), 7-5, 6-2 in the quarter-finals after one hour, 54 minutes. Bopanna and Ebden won 63 per cent of points behind their second serve, compared to their opponents’ 39 per cent.

Bopanna and Ebden, who have claimed titles in Doha and Indian Wells this year, will next clash against top seeds Wesley Koolhof and Neal Skupski after the Dutch-British duo defeated Ariel Behar and Adam Pavlasek 4-6, 6-2, 6-3 in the last eight. Koolhof and Skupski won 82 per cent of their first-serve points to advance.

The 10th seeds Kevin Krawietz and Tim Puetz downed 13th seeds Jamie Murray and Michael Venus 6-4, 6-3. The German pair will face 15th seeds Marcel Granollers and Horacio Zeballos in the semi-finals after the Spanish-Argentine team ousted Americans Nathaniel Lammons and Jackson Withrow 6-4, 7-5.

The men’s doubles semi-finals will take place Thursday on No. 1 Court, starting at 1 p.m. local time.

Novak Djokovic is a force to be reckoned with at Wimbledon, a point multiple stars of Netflix’s Break Point made in the hit tennis documentary series.

“He’s played in I have no idea how many Slam finals, probably like 30, 40,” Nick Kyrgios said. “I’m a kid from Canberra. I’m not supposed to be here. But I’m here.”

Today, Djokovic is a 23-time major winner who has reached 34 finals at Grand Slam tournaments. In last year’s Wimbledon final, the Serbian defeated Kyrgios in four sets.

“He’s so mentally in tune with everything,” Kyrgios said.

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In the final, Kyrgios made a quick start and won the opening set. From there, Djokovic took over to claim his seventh trophy at The Championships in four sets.

“His composure in certain moments where another player would have started to panic, he didn’t show me,” the Australian explained.

“He’s calmer. You can’t rush him. He’s more patient. You can’t teach that. It comes from experience.”

Two of the show’s experts, Andy Roddick and Patrick Mouratoglou, also praised Djokovic in Break Point.

“Physically dominant. Mentally tougher than everyone else,” Roddick said. “Novak, he’s the master of the game.”

Mouratoglou said of the Serbian: “Beating Novak at Wimbledon is probably the highest mountain to climb for any tennis player.”