Toronto R2 previews and predictions: Sinner vs. Berrettini, Tsitsipas vs. Monfils

A huge slate of second-round action at the Toronto Masters on Wednesday features both Jannik Sinner and Stefanos Tsitsipas. Sinner kicks off his campaign against Matteo Berrettini, while Tsitsipas runs into Gael Monfils.

Matteo Berrettini vs. (7) Jannik Sinner

It will be an all-Italian showdown when Sinner and Berrettini go head-to-head for the first time in their careers in round two of the National Bank Open on Wednesday afternoon. Berrettini opened with a 6-4, 6-3 victory over Gregoire Barrere on Monday for what was just his 11th ATP-level match win of the season. On the heels of a fourth-round performance at Wimbledon (lost to eventual champion Carlos Alcaraz in four sets), the world No. 38 is finally picking up some much-needed momentum as he returns from injury.

Sinner has been outstanding pretty much this entire year. The 21-year-old is up to No. 8 in the rankings thanks in part to a title in Montpellier, runner-up showings in Rotterdam and Miami, and a semifinal result at Wimbledon (lost to Novak Djokovic). This is not an easy matchup for Sinner especially since Berrettini already has a match under his belt in Toronto, but the seventh should be able to advance.

Pick: Sinner in 3

(4) Stefanos Tsitsipas vs. (PR) Gael Monfils

Monfils had an eventful opening match on Monday, when he should have won in straight sets but ended up going three with Chris Eubanks. Still, the 36-year-old Frenchman did well to dominate the decider after getting broken for the first time all day while trying serve out the match at 5-3 in the second. Monfils prevailed 7-6(3), 6-7(4), 6-1 to set up a fourth career encounter with Tsitsipas, who leads the head-to-head series 2-1. They have not faced each other since a 2019 meeting in Dubai, where the Greek survived a 4-6, 7-6(4), 7-6(4) thriller.

Tsitsipas is coming off a title in Los Cabos, where he dropped only one set all week and defeated Alex de Minaur 6-3, 6-4 in the championship match. That final was on Saturday instead of Sunday; combine that with a first-round bye in Toronto and the world No. 4 will have enjoyed plenty of rest in advance of this matchup. Count on Tsitsipas remaining on a roll.

Pick: Tsitsipas in 2