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LONDON — Barring upset or injury, Novak Djokovic will be eating grass in less than two weeks.

After each of his past seven Wimbledon men’s singles wins, he has dropped down to the Centre Court turf and tasted a blade of grass. It’s going to take some monumental effort, or an unfortunate event, to prevent him from repeating this on July 16 and securing his 24th Grand Slam.

But there’s another honor on his radar as well — one that has not been achieved on the men’s side since 1969.

The calendar Grand Slam is an elusive feat. Only five players in the history of women’s and men’s singles have won the Australian Open, French Open, Wimbledon and US Open in a single year, and it has been managed only three times since the start of the Open era in 1968.

Djokovic has come close twice before, only to fall short. In 2021, he was one match away from securing all four Slams that year, but lost the US Open final to Daniil Medvedev. “Never have I lived through such pressure in my career,” he said after, at the Paris Masters.

Two years later, with the Australian and French Open title already secured, Djokovic is halfway there. But with it comes that same incredible burden.

The five who’ve done it

The quest officially began back in 1925, when the four tournaments gained major status. But tennis would have to wait until 1938 for its first calendar Grand Slam to be achieved, when American Don Budge swept all four majors. Budge was also the youngest to ever hold a “Career Slam” (winning all four during his career), which he did halfway through that year when he won the French Open just before his 23rd birthday.

“He stands tall in the record books,” five-time Slam champion Tony Trabert later said of Budge. “His backhand was what we called a concluder; the sort of shot people will still be talking about a hundred years later.”

Maureen “Little Mo” Connolly was 18 years old when she became the first to collect all four women’s singles titles in 1953, remarkably dropping only one set in the process. Her career would end two weeks after she won the 1954 Wimbledon title after she suffered injuries from a horse-riding accident. But by that point she’d already secured her spot in history and with it, an early understanding of tennis burnout. “Tennis can be a grind and there is always the danger of going stale if you think about it too much,” she said. “You can get embittered if you train too hard and have nothing else on your mind. You have to be able to relax between matches and between tournaments.”

Nine years later, Australian “Rocket” Rod Laver completed all four in 1962. Then seven years later, he became the first to do it in the Open era, which began in 1968. As Laver, 30, completed the calendar Grand Slam in 1969, his mind was back in Australia with his wife, Mary. She would give birth three weeks after the US Open final, a match where Laver overcame Tony Roche (7-9, 6-1, 6-2, 6-2). “Thinking of Mary certainly eased my concerns about completing the calendar-year Grand Slam,” Laver said on the 50th anniversary of the 1969 Slam.

“If you had a champion who accomplished a record that no one else had attained in any sport, you’d have to say that champion was the greatest of all time,” Trabert said of Laver. “Rod Laver holds a record that will never be broken: he won the Grand Slam as an amateur and he won the Grand Slam again as a pro.”

A year later, Margaret Court completed her calendar Grand Slam, in 1970 on her way to the Grand Slam record of 24. Court had already come close twice, winning three Slams in 1963 and 1969, and would later win three in 1973 as well

Billie Jean King won three in a year in 1972, while Martina Navratilova collected three in 1983 and 1984, but Steffi Graf would be the next to win all four, in 1988.

Graf’s series of triumphs that year was even more remarkable because she also won Olympic gold in the women’s singles in Seoul, making her the only player in tennis history to achieve the Golden Slam. She also added a Wimbledon doubles title that year with Gabriela Sabatini. Graf went into the Olympics “tired,” by her own admission, and with few expectations. But would leave with a slice of history. “I’m very excited,” Graf, then 19 years old, said. “It’s something not many people after me will achieve. It’s amazing.”

In fact, Graf’s is the last calendar Grand Slam to date. Serena Williams, Roger Federer, Rafael Nadal and Djokovic have all come close since. And at various stages, each of the four got tired of talking about the elusive prize.

But none of the Big 3, or Serena

Federer came close to a calendar Grand Slam three times, but each time he missed out on Roland Garros. His first chance was in 2004, but his charge fell at the third round to Gustavo Kuerten. “I wish it’s going to happen,” Federer said later that year ahead of the US Open. “But I know how tough it is. To always keep it up and always beat everybody, it’s not the easiest thing to do. It’s easier to lose than to win.” In 2006 and 2007, while he managed to win the Australian Open, Wimbledon and US Open, his Paris hopes ran into a Nadal-sized obstacle in both finals.

Nadal won a Slam on all three surfaces in 2010, but he suffered a knee injury in the quarterfinals of the Australian Open, so he never had a chance at the calendar Grand Slam. He came close again in 2022 after winning the opening two Slams, but suffered an abdominal tear at Wimbledon. “I felt that playing at the level that I was playing, probably I will have a chance [of winning all four],” he said.

Williams’ greatest shot at all four was in 2015. After winning the Australian Open, French Open and Wimbledon, she headed into the US Open as overwhelming favorite. “I don’t feel that fresh pressure. If I make it far, maybe I’ll start to feel pressure,” she said early on at the tournament. Eventually, she fell to heavy underdog Roberta Vinci in the semifinals. She shut down any questions postmatch. “I don’t want to talk about how disappointing it is for me,” Williams said.

Instead she emphasized the significance of the “Serena Slam” she’d achieved for the second time — where she held all four majors but across two calendar years. “I felt very happy to get that win at Wimbledon, you know. I did win three Grand Slams this year. Yeah, I won four in a row. It’s pretty good.”

During the 2021 US Open, the world was watching Djokovic get to just one step away from winning all four. He battled through a five-setter in the semifinals against Alexander Zverev, to give himself a shot at completing the sweep in the final against Medvedev.

“I have to hit one ball at a time, try to be in the moment, have a guiding star in a way, a dream to win a Slam here which would obviously complete the calendar Slam,” Djokovic said. “I’m hugely inspired and motivated by that, no doubt.” Both Nadal and Federer were absent, so the spotlight had been solely trained on Djokovic. “I thrive under pressure,” Djokovic said. “I’ve done that many times in my career. Pressure is a privilege, it truly is.”

But it fell apart in the final, which Medvedev won in straight sets. It was only a few weeks later that Djokovic realized the strain he’d been under. “I’m not spending days suffering because I didn’t take the calendar Slam this year,” he said at the Paris Masters later that year. “I’m very relieved that the calendar, that the Grand Slam season was done, because I felt a tremendous pressure unlike anything I felt in my life.”

Federer later that year was asked about Djokovic’s attempt: “I think it is possible that [the calendar Slam is] going to happen again. With Novak, myself and Rafa that we come extremely close but just doing it, you know, I think you need a bit of luck. You need perseverance, strength, you need everything.”

Can Djokovic do it in 2023?

At Wimbledon, Djokovic will attempt to win the third Slam of the year, setting himself up for a redo of 2021. Thoughts of a potential calendar Grand Slam were soon raised after his Roland Garros win. “I’d like to get another chance in New York,” Djokovic said in Paris. “Of course, I have to win Wimbledon, which is a whole different mountain to climb. If that happens, I’d love to get a chance to go for history in New York.”

It’s on the radar of his coach, Goran Ivanisevic. “Novak is [the] only player who can win [a] calendar Grand Slam. He was one match away two years ago, so he has a chance this year,” Ivanisevic said after the Roland Garros win. “But it’s still, you know, [a] long way.”

Djokovic has tried and fallen short in the past. But as the last man standing out of the famous trio of tennis greats, and the next generation unable to stop him so far this year, this could be his greatest opportunity to achieve tennis immortality.

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Can Djokovic become the first player in 35 years to complete a calendar Grand Slam?