Jannik Sinner shows his support for girlfriend Anna Kalinskaya, cheers Russian on from the stands during her Wimbledon 3R win

Jannik Sinner was all smiles as he cheered on his girlfriend Anna Kalinskaya from the stands during her third round 7-6(4), 6-2 victory over 15th seed Liudmila Samsonova. Kalinskaya reached the fourth round at the grasscourt Major for the first time in her career.

The couple went public with their relationship in May during the French Open, where they were spotted watching each other’s matches. Sinner confirmed that he was dating Kalinskaya, but declined to give further details, saying he wanted to keep their private life confidential.

Jannik Sinner was previously linked to model Maria Braccini, while Anna Kalinskaya had dated Australian player Nick Kyrgios in the past.

At Wimbledon, they have both been in decent form, advancing to the second week of the tournament. Sinner, the top seed, has dropped only two sets in his three matches, defeating Yannick Hanfmann, Matteo Berrettini, and Miomir Kecmanovic to reach the fourth round.

Seventeenth seed Kalinskaya, meanwhile, has beat Panna Udvardy, Marie Bouzkova, and Samsonova to reach the fourth round for the first time in her career.

Wimbledon’s official X account shared a picture of Sinner smiling in the stands during the match against Samsonova, sitting alongside Kalinskaya’s coach Patricia Tarabini.

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Jannik Sinner will take on Ben Shelton while Anna Kalinskaya will face Elena Rybakina at Wimbledon R16

Jannik Sinner and Ben Shelton at the 2023 Shanghai Rolex Masters

Top seed Jannik Sinner will take on 14th seed Ben Shelton in the Round of 16 at the 2024 Wimbledon Championships on Sunday, July 7.

Shelton is the current World No. 14 and the third-ranked American singles player. The 21-year-old won three consecutive five-set matches, defeating Mattia Bellucci 4-6, 6-3, 3-6, 6-3, 6-4, Lloyd Harris 4-6, 7-6(5), 6-7(5), 6-3, 7-6(7), and Denis Shapovalov 6-7(4), 6-2, 6-4, 4-6, 6-2. Shelton aims to reach his third Grand Slam quarterfinal and his first at Wimbledon.

The two players have met three times previously, with Jannik Sinner leading the head-to-head at 2-1. However, Shelton won their first encounter 2-6, 6-3, 7-6(5) in the Round of 16 at the 2023 Shanghai Masters.

The winner of the upcoming match will face either 10th seed Grigor Dimitrov or fifth seed Daniil Medvedev in the quarterfinals.

Meanwhile, 17th seed Anna Kalinskaya will face fourth seed Elena Rybakina in the Round of 16 at SW19 on Monday, July 8.

Rybakina won the 2022 Wimbledon Championships by defeating Ons Jabeur in the final and reached the quarterfinals last year. This year, the 25-year-old has dropped only a single set so far, defeating Elena-Gabriela Ruse 6-3, 6-1, Laura Siegemund 6-3, 3-6, 6-3, and Caroline Wozniacki 6-0, 6-1.

Rybakina and Kalinskaya have met four times on the WTA tour before, with both winning two matches each. Their most recent encounter was in the third round of the 2023 Italian Open, where Rybakina received a walkover victory due to Kalinskaya's mid-match retirement due to injury.

The winner of Monday's match will take on either 21st seed Elina Svitolina or Wang Xinyu in the quarterfinals.