Two American tennis stars and close friends will clash in the Australian Open fourth round, marking the first time two podcast co-hosts face each other at a Grand Slam. Sixth seed Jessica Pegula and the defending champion and ninth seed Madison Keys both host The Player’s Box alongside Desirae Krawczyk and Jennifer Brady. After advancing through the third round with straight-set victories, they will now face off for a quarterfinals spot.
However, before the match, the two competitors discussed their playful wager, with Pegula explaining why her side of the bet is considerably worse.
Jessica Pegula Explains Why Her Part of the Wager is Worse than Madison Keys
This fourth-round encounter will be historic, as Pegula and Keys become the first podcast co-hosts to face each other in a Grand Slam match. To add stakes to their match, the two friends made a playful wager: If Keys loses, she will eat apple pie with cheese, a tradition in Pegula’s family. If Pegula loses, she must wear a Kansas City Chiefs jersey.
In the latest episode of The Player’s Box Podcast, Pegula explained why her part of the wager is far worse than Keys’.
“It’s clearly mine. Are you kidding me? My family owns the Buffalo Bills. They’ve owned it. Like, I have to sit there and wear this, and then there’s going to be pictures, and then people are going to be like ‘Jess clearly lost a bet,’ and I’m going to have to suffer. Mine is definitely worse.”
During the discussion, Pegula explained how it all started when they bumped into each other during the press. “We were walking the press, and we saw each other, and I was laughing about how they’re talking about this as the first ever podcast hosts playing each other at a Grand Slam.
“My agent was like you guys need to come up with a funny bet or something, and then I literally yelled down the hallway, ‘Apple pie with cheese on it.’ She’s like, ‘No, never.’ And I’m like, ‘Nope, I’m sticking to it,'” Pegula said.
Keys revealed how she came up with her side as payback for Pegula’s suggestion. “When you came after me for the apple pie, I was like, ‘What’s the worst thing that I could possibly think of for Jess for retaliation?'” Keys said.
The Buffalo Bills and Kansas City Chiefs’ rivalry explains Pegula’s concern, since these two NFL teams have a competitive history, and for someone whose family owns the Bills, wearing a Chiefs jersey makes it more uncomfortable.
Keys and Pegula Set for a Historic and Emotional Matchup
Keys currently leads the head-to-head record 2-1 over Pegula, having won their most recent match at the 2025 Adelaide International with a 6-3, 4-6, 6-1 victory to lift the trophy. This was Keys’ second consecutive win over Pegula, having beaten her previously in the fourth round of the 2023 US Open.
Both players step foot on the court with excellent momentum. Keys has won ten consecutive matches at Melbourne Park without dropping a single set through the third round. The defending champion beat Oleksandra Oliynykova 7-6(6), 6-1 and Ashlyn Krueger 6-1, 7-5 in her first two rounds before beating former World No. 1 Karolína Plíšková 6-3, 6-3.
Pegula has yet to drop a set at the 2026 Australian Open, with her most recent victory over Oksana Selekhmeteva taking just 67 minutes, showing her dominance on hard court. The odds are relatively tight between the two, though the PFSN’s exclusive interactive simulator favors Pegula with 61% chances of advancing to the quarterfinals.
With this match guaranteeing an American in the quarterfinals, the United States will have at least three players in the women’s singles final eight. And if Amanda Anisimova wins her fourth-round match, that would make 50% Americans in the Australian Open quarterfinals.
