“If Jess loses, she has to wear a Chiefs jersey”: Pegula and Keys’ Melbourne showdown comes with a hilarious bet

Jessica Pegula and Madison Keys are set to collide in the fourth round of the Australian Open, but the build-up to their Melbourne meeting has been defined more by laughter than tension. On The Player’s Box podcast, the two Americans openly previewed the matchup in a relaxed environment, joking around with co-hosts Jennifer Brady and Desirae Krawczyk while acknowledging the unusual dynamic of facing a close friend deep in a Grand Slam.

The conversation quickly turned playful when Krawczyk laid out the stakes of a friendly bet tied to the match. “If Maddie loses, she has to eat Jess’s favourite thing: cheese on apple pie. If Jess loses, she has to wear a Chiefs jersey,” Desirae explained, immediately triggering reactions from both players.

Pegula wasted no time making her feelings clear. “Clearly mine is worse. A Chiefs jersey. A hundred percent worse,” she said, a comment that only made more sense once the context was spelled out. Keys jumped in with the crucial detail: Pegula’s family owns the Buffalo Bills. That reality alone turned the joke into something far more serious in Pegula’s mind.

The teasing escalated as Pegula imagined the consequences. “There are going to be pictures,” she said. “People will know I lost a bet.” When the idea of alternatives came up, she briefly reconsidered. “I’d maybe rather wear a Taylor Swift shirt,” Pegula admitted, prompting Keys to double down on the visual.

Once the laughter settled, the tennis conversation revealed just how seriously both players are taking the matchup. “It’s a tough matchup,” Keys said. “We’ve played, I think, three times on the tour now in the last couple of years, and it’s gone both ways.” One encounter still stands above the rest. “We played each other last year in the Adelaide final, and it was actually a really good match.”

Keys also pointed to what makes Pegula such a constant threat week after week. “I’ve always been really impressed with how steady Jess is,” she explained. “You know she’s always going to make the best decisions, and she’s got that sneaky drop shot that you always have to be looking out for.” That consistency even became a running joke during one of Keys’ strongest stretches. “I was like, ‘I’m in my Pegula era. I just quarter every week all of a sudden.’ Jess is just always winning. She’s always there.”

Pegula remembers that Adelaide final just as clearly — and what followed only reinforced her respect. “When we played in Adelaide last year, it was a really good match. It went to three sets, and Maddie was playing some stellar tennis,” she said. Afterward, watching from the outside, she was convinced Keys was building something bigger. “Once I was out of the tournament, that was when Jenny, Des, and I were all texting that she was getting through all these tough matches with a really hard draw, and we thought she was going to win the Australian Open — and she did.”

Even scouting reports didn’t escape the playful tone. “I watched your last match,” Keys admitted. “I was scouting, watching your highlights, and you missed a hack slice forehand and you were so annoyed.” Pegula laughed at herself. “I’ve been working on it. I hope I can hit a good one tomorrow. If I win the point, I’m going to be like, ‘Yes, take that.’”

When they step onto the court in Melbourne, the smiles will fade and the focus will sharpen. But no matter the outcome — and no matter what ends up worn or eaten — Pegula and Keys have already shown that this Australian Open showdown is built on friendship, familiarity, and a rivalry that knows how to laugh at itself.

As Pegula and Keys prepare to face each other in the fourth round of the Australian Open, their upcoming clash carries a layer of familiarity that goes far beyond rankings or recent form. Long before Melbourne, Grand Slam pressure, or main-court spotlights, their stories were already quietly intertwined — something the two Americans recently revisited on The Player’s Box podcast.

Reflecting on their earliest memories, Pegula was the first to admit just how far back their connection goes — and how hazy those beginnings now feel. “Honestly, I have no idea,” Pegula said, laughing. “It was definitely very young. I’m a year older, so maybe you were 12 or 13 and I was 14.”

One of the first places that still stands out for her is Ponte Vedra, a setting that now feels symbolic rather than specific. “I remember Ponte Vedra. I feel like that was probably the first time,” Pegula recalled. “We were very young. I don’t even know if we spoke, but that’s probably when I had first been around you.”

Keys immediately connected that memory to a milestone moment for both players. “Yeah, I think that was the first WTA event we were both at. It was both of our firsts.”

At the time, neither could have known what lay ahead. Keys remembered how their names were quietly grouped together even then. “I remember everyone saying, ‘Oh, it’s also Jess’s first WTA event,’” she said, noting that despite being part of the same generation, their junior paths barely overlapped. “We had crossed paths in juniors, but not much.”

Geography played a role in that separation. “I played Southern sectionals. You played Florida,” Keys pointed out, prompting Pegula to explain why their encounters were so limited. “That’s why we didn’t cross paths much. I remember playing Sloane at Nationals, but I don’t remember playing you.”

The first match that truly stuck, however, came later — and remains a defining memory for Pegula to this day. “The first match I really remember was the Indian Wells pre-qualifying,” she said, with Keys quickly confirming, “Yes.”

That week proved pivotal for both. Pegula still recalls the mixture of competitiveness and frustration that came with their meeting in the final. “We played in the finals, and I was so salty because I won, but we both ended up getting wild cards,” she admitted. “I got the No. 1 seed in qualifying, and you got a way better draw.”

Keys’ response was simple and telling: “I qualified.”

For Pegula, that tournament marked her first true breakthrough. “That was the first big tournament I ever qualified for,” she said. “And we both got wild cards for making the finals of the pre-qualifying event. We killed everybody in the draw, and it was just us in the final.”

Years later, with both players firmly established on the WTA Tour, that match still resonates. “That was probably the first time we played and a core memory for me,” Pegula reflected.

Now, instead of pre-qualifying courts, Pegula and Keys meet in Melbourne, with a place in the Australian Open quarterfinals on the line.