Stefanos Tsitsipas is preparing to rebuild a “mature” and “strict” coaching relationship with his father, Apostolos Tsitsipas, following a period of separation. The Greek player, currently ranked world No. 30—the lowest since 2018—has endured a string of disappointing results this year after winning the ATP 500 event in Dubai in February.

Earlier in 2025, Tsitsipas began coaching with 2001 Wimbledon champion Goran Ivanisevic, but the partnership ended mutually after a first-round retirement at Wimbledon led to critical remarks from Ivanisevic. Tsitsipas and his father had originally parted ways as coach and player in late 2024.

Reflecting on their previous split, Tsitsipas told Ziggo Sport, “It was a very difficult ending, the way it ended last year with him. He managed to get me to a point that I honestly didn’t even recognize myself, the way it ended and the way I reacted to this relationship, partnership that we formed over the last couple of years, the way it ended was very obnoxious and unexpected that it would happen in that way, in that fashion.” He acknowledged regrets over his own responses, noting, “There are a lot of things that I wouldn’t want to repeat because even my behaviour and my reaction to it wasn’t very mature or wasn’t very me.”

Since then, the two have spent time together, with Apostolos present on the tour occasionally in the role of father rather than coach. Tsitsipas highlighted the need for clear boundaries, saying, “I think I have to be strict with him. Sometimes I feel like he wants to do too many things on his own. I’m trying to recalibrate that and make him understand that it’s also certain things need to happen the way I want them to happen. I think this relationship deserves way more than the way we’ve been treating it in the past.”

Tsitsipas is set to return to competition at the Canadian Masters, facing either Christopher O’Connell or Tseng Chun-hsin in the second round. He has not won consecutive matches in over three months and retired in his opening-round Wimbledon match due to persistent back pain, an issue dating back to the 2023 Nitto ATP Finals.

On his physical condition, Tsitsipas shared, “I’m feeling much, much better. I wouldn’t have imagined that three weeks ago I would be in the position I am now because I was in a really bad state, physically mainly. But we all know that once you’re physically not there, it affects the other chain too. It affects you mentally, it affects you in all kinds of ways and forms. In a situation like this, I just need to stay strong. I’m happy I’m in Toronto, it was not part of the plan. It’s been a tumultuous period.”

The National Bank Open in Toronto will feature an intriguing showdown between two emerging talents, Joao Fonseca and Tristan Schoolkate, showcasing players on distinct paths in professional tennis. Fonseca, the 18-year-old Brazilian prodigy, has rapidly ascended the ranks with a spot in the Top 50, a tournament title, and a 15-11 record this season. Traveling full-time on the main ATP Tour, he is seen as a rising star poised for continued success.

Schoolkate, at 24, represents a different journey. The Australian has primarily competed on the ATP Challenger Tour and through qualifying rounds, traveling globally to events from Pune to Cary, NC. Just outside the Top 100 at No. 103, he has yet to claim an ATP title but gained attention by taking a set from Jannik Sinner at the Australian Open, one of only two sets Sinner dropped in that major.

Their meeting at Toronto marks Schoolkate’s fourth tournament following Wimbledon, including a brief return to grass in Newport. Both players employ a contemporary baseline style characterized by effective flat and kick serves, strong topspin forehands, and two-handed backhands. Fonseca’s forehand stands out as his primary weapon, while Schoolkate’s backhand, capable of penetrating down the line, is key to his game.

This match offers a compelling contrast: Fonseca on the rapid rise in the main draw spotlight, and Schoolkate battling upward through the ranks with persistence and moments of significant play. Fans can catch live coverage on TennisChannel.com starting at approximately 12:30 p.m. ET on Monday, July 28, where the full National Bank Open bracket is also accessible for viewing.

Naomi Osaka is set to play against Canadian qualifier Ariana Arseneault in the first round of the Montreal tournament. Arseneault, a 23-year-old from Ontario and former U.S. college player, currently holds a singles ranking of 515, just shy of her career best by four spots. While she has found more success in doubles with a ranking of 122, Arseneault will face a formidable challenge against Osaka, a former world No. 1.

Canadians have generally performed well at their home event over the past decade, providing some encouragement for Arseneault as she approaches this match with little to lose. The encounter is scheduled to begin at approximately 1:40 p.m. ET on Monday, July 28, and will be available for live coverage on TennisChannel.com.

Osaka, known for her top-ranking status and Grand Slam titles, will be the favorite against the qualifier. For those interested, the complete Montreal tournament bracket is accessible online, offering insights into potential matchups and progressions.

This match highlights the contrast between Osaka’s experience at the highest level of tennis and Arseneault’s ongoing rise through the ranks, making it an interesting contest to watch.