Novak Djokovic won’t be in action at the Toronto Masters this year. The four-time champion has pulled out of the event following a groin injury that came after his semifinal loss to Jannik Sinner at Wimbledon. At 38, the Serbian is beginning to pick his battles, and lately, that means skipping smaller tournaments to focus on the Grand Slams. But his absence also comes with a bittersweet twist. This week in Toronto will mark the final professional appearance of his longtime friend and fellow player, Vasek Pospisil. Djokovic won’t be there in person to say goodbye, but he has already made sure his support is felt.

“Eighteen years of professional tennis. Looking forward to playing in front of you one last time in Toronto,” Pospisil wrote on social media. The 35-year-old Canadian will retire after this tournament, closing the book on a career that saw him reach No. 4 in doubles and No. 25 in singles. He won the Wimbledon men’s doubles title in 2014 with Jack Sock and helped Canada clinch the Davis Cup in 2022.

Novak Djokovic took to his Instagram Story to show his appreciation. He posted a simple but heartfelt combination of emojis: “🙌 🙏 💪 👏 🇨🇦.” The message may have been brief, but it carried weight, especially given the history between the two.

Their friendship isn’t just built on years of competing on tour. Djokovic and Pospisil have shared a deeper bond since 2020, when they co-founded the Professional Tennis Players Association. The PTPA was created to give players more collective power and advocate for improved conditions across the sport.

The PTPA made headlines earlier this year with an antitrust lawsuit that took aim at tennis’s major governing bodies. The lawsuit, filed in March, described the sport’s leadership structure as a “cartel” that allegedly suppressed player wages, limited opportunities, and blocked rival tournaments. The accused organizations have denied the claims and recently filed motions to dismiss the case.

While Pospisil is named as a plaintiff in the case, Djokovic is not. Speaking at the Miami Open, the Serb shared his mixed feelings about the lawsuit. “To be quite frank with you, there are things that I agree with in the lawsuit and there are also things that I don’t agree with,” Djokovic said. “I found that maybe some wording was quite strong in there.”

Even with their differing views on certain parts of the legal action, their friendship has stayed strong. Novak Djokovic made sure to send his support as Pospisil prepared for his farewell. And now, as the Canadian plays his final match, one of his closest allies will be cheering from afar.

As Pospisil steps away, many fans and experts are wondering how much longer will the 24-time Grand Slam keep going.

Tennis insider hints at impending Novak Djokovic retirement

After his Wimbledon exit to Sinner, the retirement talk picked up once again. But Novak Djokovic shut it down immediately. “I’m not planning to finish my Wimbledon career today. I’m planning to come back definitely, at least one more time,” the 38-year-old said in his post-match press conference. That statement was enough to hold off the rumors, but not everyone is convinced he’ll be around much longer.

Veteran tennis journalist Steve Flink weighed in recently on Gill Gross’s YouTube channel. “It’s going to be fascinating to see what he can summon for the U.S. Open,” Flink said, pointing to the possibility that a poor result in New York might push Djokovic to reconsider his future. “I think Novak can accept these last three; he’s a little disappointed but proud to be in the semifinals,” Flink said. “I think if he came to New York and didn’t go that far and had a surprising loss in the round of 16, then I think he might think seriously to say there is no point.”

Novak Djokovic is a four-time U.S. Open champion, having won the event in 2011, 2015, 2018, and 2023. But his title defense ended early last year with a surprise third-round loss to Alexei Popyrin, while Sinner went on to lift the trophy.

Toronto won’t see Djokovic this time, but the rest of the season could still bring one more big moment. Can the 38-year-old summon another Grand Slam win? What do you think?