The Round of 32 is underway at the National Bank Open in Toronto, and Friday's slate on the hard courts delivers a strong mix of seeded veterans and rising contenders. From an intriguing first-time meeting to a rivalry with eleven prior encounters, the day's matches offer plenty of compelling storylines drawn directly from the head-to-head record books.

Ann Li vs. Elena Rybakina - Round of 32

Scheduled for approximately 3:35 PM EDT, this Round of 32 clash brings together world No. 29 Ann Li and No. 2 Elena Rybakina. These two have never previously met, making this a true unknown on paper. Rybakina's ranking advantage is substantial, but Li's top-30 standing means she is no pushover stepping into this encounter for the first time.

Prediction: Elena Rybakina

Mirra Andreeva vs. Leylah Annie Fernandez - Round of 32

Scheduled for approximately 5:05 PM EDT, world No. 5 Mirra Andreeva faces No. 22 Leylah Annie Fernandez in a Round of 32 contest with a familiar history. Andreeva leads their head-to-head 2-1, with her two wins coming at the Mutua Madrid Open, including a 6-3 6-4 victory in the Round 1 and a 7-6(1) 6-3 result in the Quarterfinal. Fernandez's lone win over Andreeva came at the Hong Kong Tennis Open with a 3-6 6-1 6-3 comeback, showing she is capable of reversing the trend when she gets into longer battles. Andreeva's Madrid record in this matchup gives her a clear edge on the head-to-head ledger heading into Toronto.

Prediction: Mirra Andreeva

Elise Mertens vs. Naomi Osaka - Round of 32

No. 24 Elise Mertens and No. 15 Naomi Osaka meet in the Round of 32 with Osaka holding the overall head-to-head edge at 5-3. Osaka has won three of the last five meetings, including straight-set semifinal victories at the Toray Pan Pacific Open (6-4 6-1) and the Western and Southern Open (6-2 7-6(5)), as well as a 6-3 6-3 win in the Round 4 of the Miami Open. Mertens has shown she can break through, winning at the Wuhan Tennis Open (6-4 1-6 6-4) and the BNP Paribas Open in Indian Wells (7-5 6-4), but the overall ledger favors Osaka.

Prediction: Naomi Osaka

Jessica Pegula vs. Katerina Siniakova - Round of 32

World No. 4 Jessica Pegula takes on No. 34 Katerina Siniakova in the Round of 32, with Pegula holding a commanding 6-1 head-to-head advantage. Pegula has won four of the last five meetings, including a 6-4 6-3 victory at the Citi Open in Washington, a 6-3 6-2 result at the Qatar TotalEnergies Open in Doha, and a 7-6(2) 3-6 6-3 win at the Berlin Ladies Open. Siniakova's sole win in the series came at the Bad Homburg Open with a 6-3 5-7 6-4 result, but the weight of the head-to-head record points firmly in Pegula's direction.

Prediction: Jessica Pegula

Maria Sakkari vs. Cori Gauff - Round of 32

No. 41 Maria Sakkari and No. 7 Cori Gauff bring one of the closest rivalries on the day's slate to the Round of 32, with Gauff holding a narrow 6-5 edge in their eleven prior meetings. The last five results have been split 3-2 in Sakkari's favor, including wins at the Abu Dhabi Tennis Open (7-5 6-2), the Qatar TotalEnergies Open Quarterfinal (6-3 6-3), and the Internazionali BNL d'Italia Round 3 (6-4 7-5). Gauff countered with wins in the Rome Round 2 (6-1 1-6 6-1) and the Mubadala Citi DC Open Final (6-2 6-3), demonstrating she can close out big matches against Sakkari. The near-even overall record and Sakkari's recent momentum make this one of the day's most difficult calls.

Prediction: Maria Sakkari