Novak Djokovic's campaign at the Madrid Open 2025 concluded with a 6-3, 6-4 loss to Matteo Arnaldi. It marked the first time he exited two consecutive tournaments on clay without winning a match. He left the Monte-Carlo Masters without a win as well a couple of weeks ago.
Djokovic has also lost three matches in a row for the second time this year. His current streak started with a loss to Jakub Mensik in the Miami Open final. He previously lost three consecutive matches starting with his mid-match retirement in the semifinals of the Australian Open.
The 37-year-old's inconsistency this season is unusual by his lofty standards. Murmurs of an impending retirement are also getting louder with every loss. Seeing an all-time great player struggling to put together some wins is neither a fun experience for the player nor the fans. So the question remains, should Djokovic continue in his quest for glory or walk away having already accomplished everything there is in the sport?
Two other legends of the sport, Serena Williams and Steffi Graf, approached this in contrasting ways. The American won her 23rd Major title while being pregnant at the Australian Open 2017, setting a new Open Era record. However, she returned post maternity leave in order to equal or better Margaret Court's all-time record of 24 Major titles.
Williams put herself in a position to do so on four occasions but nerves got the better of her. She massively underperformed by her high standards in the four Major finals, two each at the US open and Wimbledon in 2018 and 2019, upon her comeback. She didn't reach another final after that and the losses started to pile up.
Yet, Williams continued playing until an injury at Wimbledon 2021 effectively heralded the end of her career. She skipped the remainder of the season and returned for a brief farewell tour in 2022. She contested the last match of her career at the US Open, going out in the third round with a three-set loss to Ajla Tomljanovic.
Seeing Williams struggle even prior to her last big injury wasn't enjoyable. However, one cannot fault for players wanting to go out on their own terms. Graf, on the other hand, was quick to call it quits once she realized she wasn't cut for tennis anymore.
Novak Djokovic finds himself in the same position as Steffi Graf did before her retirement

Recurring injuries bothered Steffi Graf in the late 1990s. She finished the 1996 season on a high, winning three Major titles and clinching the year-end No. 1 ranking. She competed in only five tournaments in 1997 and ended the year ranked 28th, her first finish outside of the top 10 since 1984.
Graf returned to the top 10 in 1998 but didn't win a Major that year, or any other big titles for that matter. Heading into the 1999 season, she hadn't reached a Major final since the US Open 1996. She rolled back the years with a title-winning run at the French Open 1999, her 22nd Major title. She also finished as the runner-up at Wimbledon a few weeks later.
Those two results gave Graf some motivation to continue but the desire vanished after she picked up another injury. She injured her hamstring in August while competing at a tournament in San Diego. She finally had enough of the tour and announced her retirement soon after that.
Graf stated that she wasn't looking forward to competing anymore following her Wimbledon run. The competitive fire within her had diminished and coupled with recurring injuries, she felt that it was the right time to call it quits.
Novak Djokovic is in the same boat as Graf. The latter shattered many records back then. She held the Open Era record for most Major titles until Serena Williams surpassed her. The German remains the only player in the sport to complete a Golden Calendar Slam and still holds the record for most weeks at No. 1 on the women's tour.
Djokovic holds the sole record for most Major titles among men and shares the all-time record with Margaret Court. He has spent a record 428 weeks at the top spot and won 40 Masters 1000 titles. An Olympic gold was the only missing prize in his trophy cabinet, which he finally secured at last year's Paris Olympics.
Retiring after his triumph at the Paris Olympics would've been an amazing way for Djokovic to go out. The gold medal was the most coveted prize for him and bidding farewell to the sport after accomplishing his most cherished goal would've been a great way for him to wrap up his career.
Djokovic has continued to soldier on since then. He has produced some good results since his run at the Olympics, reaching the finals of the Shanghai Masters and the Miami Open. However, he seems to be dealing with a sense of self-doubt these days after some underwhelming results this year.
The 37-year-old expressed his frustration during a practice session at the Madrid Open. Following his loss, he was quite upset during his press conference and was coming to terms with the reality of winning a match or two, instead of going deep in every tournament.
"Kind of new reality for me, I have to say. You know, trying to win a match or two, not really thinking about getting far in the tournament. It's a completely different feeling from what I had in 20-plus years of professional tennis," Djokovic after his loss in Madrid.
The lure of a record 25th Major title and a 100th career title is extremely tempting. Unlike many other greats of the sport who were ravaged physically towards the end of their careers, Djokovic is still in pretty great shape. However, if he continues to suffer early exits repeatedly in the future, calling it quits after a great run in between would be the ideal way for him to go, something akin to what Graf did back in the day.
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