Jessica Pegula and Madison Keys, co-hosts of The Player’s Box podcast, entered a friendly wager before their fourth-round clash in the 2026 Australian Open. Pegula, the daughter of Buffalo Bills owner Terry Pegula, won the match 6-3, 6-4, and avoided a cardinal sin.
According to the wager, had Pegula lost, the Buffalo Bills’ heiress would be required to wear the jersey of Kansas City Chiefs tight end Travis Kelce’s fiancée, Taylor Swift’s jersey. The Bills and the Chiefs have been arch-rivals in the playoffs over the last four seasons in the NFL. More often than not, it has been the Chiefs who have got the better of Pegula’s Bills. Thus, it would have been a cardinal sin to wear a jersey of an arch-rival.
Pegula defeated defending Australian Open champion Keys, who, as part of the wager, had to eat apple pie with a piece of cheddar cheese on top of it. Pegula mentioned this was a Canadian tradition, something her grandparents did.
“She wanted me to wear a Kelce-slash-Taylor Swift Chiefs jersey,” Pegula said in the post-match interview. “So, honestly, I had a lot of motivation today not to wear that. We’re still going strong, so that’s good. Maybe she’ll eat some pie next time while we do this.”
Pegula also went on to sign the camera, writing:
“No Chiefs jersey today.”
Jessica Pegula Advances to QF After Madison Keys Win
Jessica Pegula defeated the ninth seed, Madison Keys, to advance into the quarterfinals of the tournament. The match at Rod Laver Arena saw Pegula win four out of five break points while allowing the defending champion to win only two break opportunities.
“I’ve been playing really well, seeing the ball, hitting the ball really well this whole tournament, and I wanted to stay true to that,” said Pegula. “Then just lean into a couple things that I felt like she would do, and I felt like I came out doing it pretty well. When I had the lead I tried to stick with that as much as I could. Even when she got a little rhythm back, I just really tried to focus on what I needed to do and patterns to look out for.”
Before this matchup, Pegula had a losing head-to-head record in the previous three encounters. But she leveled up on Sunday.
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