Sports Is Cruel: Dimitrov’s Heartbreak, Sinner Advances, And Wimbledon Keeps Twisting

Wimbledon’s Round 4 reminded us of something no sports fan ever wants to admit: sometimes, the better player doesn’t win.

Grigor Dimitrov was two sets up on World No. 1 Jannik Sinner and playing the match of his life—until injury struck. What followed was one of the most emotionally crushing scenes of this year’s tournament. In this episode of Ground Pass, Nick and I walk through the brutal moment Dimitrov collapsed on serve, the history of his injury record at Slams, and what it means for both players moving forward.

Elsewhere in the draw, Ben Shelton kept his winning record against Lorenzo Sonego, and Flavio Cobolli stunned with a clean run to the quarters. On the women’s side, Mirra Andreeva dazzled on Centre Court in front of Roger Federer, Iga Swiatek found another gear, and Amanda Anisimova battled through a tough three-setter.

We also revisit an odd moment in the Kartal–Pavlyuchenkova match where the electronic line-calling system mysteriously stopped working—adding to the day’s sense of “is this really happening?”

Sports is cruel. But we’re still watching. And we’ll be here all tournament long to help you make sense of it.

ICYMI: I am on the ground at the Hall of Fame Open in Newport. Follow my behind-the-scenes coverage of the tournament on our Substack with Ground Pass On Site. It’s free to subscribe, with bonus perks for paid members who want to support independent tennis media.

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