In what could be the penultimate tournament of her career, 23-time grand slam champion Serena Williams takes on US Open champion Emma Raducanu in Cincinnati.

Potentially two more tournaments to go before a legend of the sport retires in the form of Serena Williams.

Williams began her farewell tour in Toronto where she went out in the second round to Belinda Bencic and will look to make a bigger impression in Cincinnati.

However an intriguing task awaits in her opening match in Ohio as she will take on US Open champion Emma Raducanu in the opening round.

Raducanu enters the match in uninspiring form having reached the quarter-finals in Washington before an opening round exit against Camila Giorgi in Toronto.

It will be interesting how this match fairs as Williams gets a taste of facing the younger generation before she departs the sport.

That match is in a packed part of the draw where the winner of that match will play the winner of Kaia Kanepi and Victoria Azarenka.

There is also a huge match between Bianca Andreescu and Camila Giorgi with the winner taking on seventh seed Jessica Pegula in the second round.

As for Serena’s sister, Venus Williams, she hasn’t fared much better with her draw as she takes on 14th seed Karolina Pliskova in her opening round.

Also in this section of the draw is fourth seed Maria Sakkari who takes on either a qualifier or Alison Van Uytvanck.

Other highlights of the bottom half of the draw will see Sofia Kenin take on Shelby Rogers while Amanda Anisimova takes on Daria Kasatkina.

Naomi Osaka is also in the bottom half of the draw where she takes on Shuai Zhang.

Meanwhile in the top half of the draw Iga Swiatek will look to bounce back after an early exit in Toronto as she takes on Sloane Stephens or Alize Cornet in her opening round.

Other exciting matches in the top half of the draw sees Simona Halep take on Karolina Muchova while Beatriz Haddad Maia takes on Jelena Ostapenko.

Here is the full Women’s singles draw with Serena Williams expected to play on Monday night:

Casper Ruud only dropped three games against Felix Auger-Aliassime to reach the semi-finals in Montreal.

The Norwegian is into the semi-finals in Canada after a dominant performance over home favourite Felix Auger-Aliassime.

Ruud dominated from the start of the match as he produced a sublime performance only committing nine unforced errors throughout the match to reach the last four.

Ruud has had a good season on hard courts this season and is looking to make his second consecutive hard court Masters 1000 final after reaching the final in Miami.

Speaking after the match Ruud admitted he got a bit lucky but is happy to be in the last four in Canada, “It was one of those days where everything goes in one favour and luckily it was in my favour,” Ruud told the ATP website.

“With a player like Felix, you need to rely on some margins going your way. I didn’t expect them to all go on my side. It was a bit of a difficult start. I got broken but then was able to turn everything around. I hit my spots, made the shots I needed to and make him hit a lot of balls. That was the game plan and it worked well.

“The last hard-court tournament I played in was in Miami where I reached the final. I wanted to make a deep run here. I didn’t think it was too likely, being the first hard-court tournament back, but I have been playing great from the first point in the first match.”

Ruud will look to claim his first Masters 1000 title this week and rise to four in the world in the ATP rankings.

Next for Ruud is the only Masters 1000 champion left in the draw in the form of Hubert Hurkacz.

Hurkacz defeated the in-form Nick Kyrgios 7-6(4) 6-7(5) 6-1 to reach the semi-finals in Canada.

The eighth seed produced some big-serving and bold decision making as he reached his first semi-final since winning the Halle title.

Heading into their match, Ruud leads the head-to-head 1-0 where the Norwegian was victorious at Roland Garros this year.

Mixed results for British hopefuls

Meanwhile it was a mixed night for British players as Dan Evans reached his second career Masters 1000 semi-final while Jack Draper exited the tournament in the last eight.

Evans defeated Tommy Paul 1-6 6-3 6-4 to reach a landmark moment in his career in Montreal.

After his win Evans described the win as ‘extra special’ as he looks forward to a semi-final meeting with Pablo Carreno Busta, “The crowd, that’s what they buy their tickets for. That’s live sport,” Evans told the ATP website.

“You never know what’s going to happen. It was an amazing match, amazing atmosphere. I played on the court before. In the day it was amazing, but at night, there’s something about playing sport at night, it’s extra special.”

Evans will now play Carreno Busta in the last four after the Spaniard defeated British qualifier Jack Draper 7-6(4) 6-1.

Draper defeated Stefanos Tsitsipas earlier in the week but was no match for the resilient Spaniard.

Saturday’s semi-final will be the first meeting between Evans and Carreno Busta.

The singles and doubles semifinals will be played on Saturday in Canada.  In Montreal, a new men’s singles champion will be crowned, and Hubi Hurkacz is the only semifinalist to have previously won a Masters 1000 event (Miami, 2021).  Hurkacz is also in the doubles semifinals, so it will be a busy day for Hubi.  In singles, he faces a finalist from this year in Miami, Casper Ruud.

In Toronto, Simona Halep is the only former champion remaining, and is two wins away from her third title at this event.  On Saturday, she plays Jessica Pegula, who is into the semifinals in Canada for the second straight year.  Like Hurkacz, Pegula is also in the doubles semifinals.  She’s teaming with Coco Gauff, who will become the new doubles No.1 if they win the title.

Each day, this preview will analyze the two most intriguing matchups, while highlighting other notable matches on the schedule.  Saturday’s play gets underway at 12:00pm local time in Montreal and 1:00pm in Toronto.

Hubert Hurkacz (8) vs. Casper Ruud (4) – Not Before 3:00pm on Court Central in Montreal

Hurkacz ended the winning streak of Nick Kyrgios on Friday, taking him out in three sets for the second time this season.  But Ruud was even more impressive on Friday, bouncing back from a marathon victory on Thursday over Roberto Bautista Agut to overwhelm Canada’s Felix Auger-Aliassime, dropping only three games.  Predominantly known as a clay court player, Casper is also establishing himself as a considerable threat on hard courts.  That’s especially true in North America, where Ruud has claimed 16 of his last 19 matches.  But Hubi’s success on this surface remains superior, as does his serving prowess.  While Ruud prevailed in their only previous encounter, just a few months ago at Roland Garros, Hurkacz is the favorite on a hard court.

Jessica Pegula (7) vs. Simona Halep (15) – 1:00pm on Centre Court in Toronto

Halep has been dominant through four rounds this week, advancing without the loss of a set.  Simona has quietly put together a strong record of 36-10 this season, though she’s yet to achieve a big result, with only one title at the 250 level at the start of the year.  Pegula only dropped one set this week, to defending champion Camila Giorgi.  And similar to Halep, she’s accumulated a solid record this year (29-14) without winning a title.  This will be the first career meeting between these two players.  Considering Halep is now 25-6 lifetime at this event, and the way in which she has easily prevailed all week, her superior movement and defense should be enough to reach her fourth final in Canada.

Other Notable Matches on Saturday:

Pablo Carreno Busta vs. Dan Evans – Carreno Busta has played superbly this week, eliminating the likes of Jannik Sinner and Matteo Berrettini without losing a set to this stage.  Dan Evans has survived two grueling three-setters in as many days.  This is their first career meeting.

Beatriz Haddad Maia vs. Karolina Pliskova (14) – Haddad Maia has earned three big wins across the last three days over Iga Swiatek, Belinda Bencic, and Leylah Fernandez.  Pliskova is looking to reach the Canada final for the second straight year.  They have split two previous encounters, both on hard courts.

Saturday’s full Order of Play is here.