From heartbreak to hindsight, humor is how Jessica Pegula is seeing things. Five months ago, the American faced a heartbreaking R1 exit at Wimbledon. She lost to world No. 116 Elisabetta Cocciaretto, 6-2, 6-3, in just 58 minutes as the third seed. That’s the kind of match you might want to block from memory. But Pegula isn’t one to hide from a loss. She has her own way of handling tough moments.

On Tuesday, November 11, the American took to X to share her reaction to the latest episode of The Player’s Box Podcast, which she co-hosts with Madison Keys, Jennifer Brady, and Desirae Krawczyk. Pegula tweeted, “I am crying @jennifurbrady95 💀” in response to a clip of the group looking back on their Slam predictions from earlier in the year.

Earlier, they predicted Pegula would win the AO 2025. Trying to keep the magic going, Brady texted Pegula, as Brady remembered on the podcast, “I was like ‘I think you’re winning Wimbledon.’ This was after the French. This was after you lost to the French. And I was like I think you’re winning wimbledon. You’re going to be fresh as a daisy and I put a daisy emoji, like a flower emoji. Like, you’ll be locked in ready.” But, as Pegula said bluntly on the episode, “First round L.”

The magic stayed away, but it led to a great laugh as the group of pros cracked up on camera. Not to mention that one Slam didn’t define Jessica Pegula’s year. She lifted trophies in Bad Homburg, Charleston, and Austin. Her US Open run ended in the semifinals, with Sabalenka beating her. But Pegula still put together an impressive season.

Pegula just finished her year at the WTA Finals. She made it through the group stage and into the semifinals before losing to the eventual champion Elena Rybakina. Still, there is one thing Jessica Pegula says she would do differently this season.

The wish that lingers for Jessica Pegula

Her run at the WTA Finals ended in the semifinals, but she had already lost once in the group stage, against Aryna Sabalenka. Over the past 18 months, their battles on court have felt like more than just matches. The World No.1 has crossed Pegula’s path on her way to two Grand Slam titles and a couple of WTA 1000 wins since early last season.

On Tuesday at the WTA Finals, Sabalenka edged Pegula again, 6-4, 2-6, 6-3. It was their second showdown in this high-stakes event. Pegula was ahead in the final set but just missed closing it out. Their head-to-head now reads 9-3 in favor of Sabalenka, with the last three meetings all nail-biters that went to three sets.

Despite the losses, Jessica Pegula appreciates the quality of their clashes. “I do think we have really great matches, memorable matches,” she said. “I wish I won more of them … even my coaches were saying, whenever you guys play, you bring out such a high level in each other. I don’t love losing, but if you asked me in 10 years, I’d say it’s pretty cool to have these memorable matches. I just wish I won more.”

With the season done, Pegula now heads into the off-season ready to recharge. Could she take all those tough lessons from this year and flip the script in 2026?