Day Four is here at the 2023 Canadian Open with Last 16 ties the schedule for the day as the first Quarter-Finals will be set up. As ever for the National Bank Open, TennisUpToDate will preview the top ties and main talking points.

Ties include Carlos Alcaraz - Hubert Hurkacz, Andy Murray - Jannik Sinner and Lorenzo Musetti - Daniil Medvedev as the action begins to reach the business end.

Two of tennis' bright hopes will look to reach the Quarter-Finals with two spoilers looking to stop that happening as World Number One, Carlos Alcaraz after seeing off Ben Shelton in his opener returns 24 hours later to face Hubert Hurkacz. Miomir Kecmanovic and priorly Alexander Bublik were seen off by the Pole. He bounced back after a poor loss to Michael Mmoh in Washington.

Head to Head wise though in a similar tournament, Alcaraz won their only meeting in Miami last year 7-6(5), 7-6(2) to reach the final and it will likely be a close encounter again on Thursday night. As will the evergreen Andy Murray facing off against Jannik Sinner.

Murray defeated Max Purcell, the slayer of Canadians to reach this point with back to back Last 16 runs following a good week in Washington. A player that amid the backdrop of media asking about his retirement all the time continues to show that he still has fight, desire and the game to match.

He now faces Sinner who will look like Murray to win Grand Slam titles and ascend to the top of the sport. He defeated Matteo Berrettini last round and takes a 1-1 Head to Head into his battle with Murray. It is a meeting every year with Sinner taking the only one on Outdoor Hard last year in Dubai.

The other top clashes see Mackenzie McDonald face off against Milos Raonic, with the latter continuing his fairytale story back home for the first time in 8 years. While McDonald will look to be the giant killer once more, he dumped out Andrey Rublev yesterday and will look to add another top name to his tally.

As will Lorenzo Musetti with the new look Italian using his new haircut as a good omen. He faces Daniil Medvedev in the second match up on the Centre Court before Alcaraz and Murray take Centre Stage and will look to make a statement of his own.

Other ties feature Alejandro Davidovich Fokina who has laid to waste the chances of J.J Wolf and Alexander Zverev in little time at all. Next up is Casper Ruud. Taylor Fritz will take on Alex de Minaur, while after lopsided results, it is Gael Monfils facing Aleksandar Vukic. As Tommy Paul finally will not face Holger Rune but instead Marcos Giron.

R16 Mackenzie McDonald VS Milos Raonic

R16 Lorenzo Musetti VS Daniil Medvedev

R16 Carlos Alcaraz VS Hubert Hurkacz

R16 Andy Murray VS Jannik Sinner

R16 Alejandro Davidovich Fokina VS Casper Ruud

R16 Taylor Fritz VS Alex de Minaur

R16 Gael Monfils VS Aleksandar Vukic

R16 Tommy Paul VS Marcos Giron