Jessica Pegula vs. Maria Sakkari: Where to Watch, Montreal Preview

The American and the Greek know each other well. They’re 31 and 30, respectively, and have played 11 times dating back 2019. Pegula leads 6-5, and has won their last three matches—including one in 2025 in Adelaide—without dropping a set.

Once upon a time, at the start of this decade, these two scaled the rankings together. But only Pegula remains at the top. She’s No. 4, with a gaudy 35-14 record in 2025 and three titles on three surfaces. She’s also the two-time defending champion in Canada. Sakkari, meanwhile, is ranked 72nd, and will bring a losing mark—19-21—to this match.

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HIGHLIGHTS: Jessica Pegula hits reset button to topple Amanda Anisimova in Toronto final

What chance does Sakkari have of reclaiming her glory years, when she won four of her first five meetings with this opponent? She’s still one of the tour’s great athletes, and she shows signs of her old self in patches—last week in D.C. she beat No. 2 seed Emma Navarro. But overall, she’s just not consistent enough now.

Pegula has taken a few bad and surprising losses this year, including in the first round at Wimbledon. But here she’ll be playing an opponent she knows well, on a court she likes, with a lot of ranking points she wants to defend. Winner: Pegula

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