Think you know your favorite athletes? You’ve seen them on the court, but what about the mishaps, late nights, and unexpected encounters that happen before the game starts? Step inside the world of tennis with Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk as they pull back the curtain on life behind the scenes. From breaking down the game to sharing wild travel stories, pop culture takes, and plenty of fan Q&As, it’s your all-access pass to life beyond the baseline. The Players Box drops every Tuesday—grab your seat courtside.
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Sep 29, 2026 · 1:03:07
This week might be one of the most chaotic weeks in Player’s Box history. Someone needs to run Jenny through concussion protocol, Jess is gaslit, Madi is offended and Des is up…
Sep 22, 2026 · 51:02
This week on The Player’s Box ice cream melted, someone tried to fill up an electric car with gas, someone got burned and someone lingered. You be the judge! We also discuss all…
Sep 15, 2026 · 1:04:23
This week on The Player’s Box Jenny has car karma, go to Jess if you’d like museum tickets she probably has extra, Des attempted an art project and Madi is living in windshield…
Sep 6, 2026 · 1:00:19
In honor of football Sunday, we’re dropping this episode a little early. The entire Player’s Box team pulled off the surprise of the podcast bringing Josh Allen in to surprise…
Sep 1, 2026 · 58:44
The Player’s Box is live this week to kick off the US Open and half the pod almost didn’t make it since Jenny’s plane almost ran out of fuel (at least it wasn’t a car) and Des…
Aug 25, 2026 · 59:10
This week we walk down a year of memory lane on the pod with Jenny’s bloopers, Madi’s anti-lingering, Jess’s tech issues and Des trying to get us cancelled and yet we’ve never…
Aug 18, 2026 · 48:36
This week on The Player’s Box we’re just going to stop letting the group chat leave the house because there’s food spilled all over the grocery store, drinks spilled on…
Aug 11, 2026 · 49:15
This week on The Player’s Box Madi received the world’s most expensive pack of Clorox wipes, Jess returns to the Florida DMV (iykyk), and Jenny gives Des a new last name. Thank…
Aug 4, 2026 · 1:00:02
This week on The Player’s Box we are anti-slipper as they caused Jenny to get strep throat and Jess to step on glass. Madi was ready to call anyone and everyone involved in a…
Jul 28, 2026 · 52:54
This week on The Player’s Box Jenny is in a club with slippers, Des killed all of her plants, Jess lost multiple iPad cases multiple times and Madi didn’t sleep for basically two…
Jul 21, 2026 · 57:41
This week on The Player’s Box Des is a reckless child while Jenny has no tolerance for her reckless ways, Jess hate deleted her own Instagram comment (or did she…) and Madi has…
Jul 14, 2026 · 1:06:01
This week on The Player’s Box, we hope Des’s car rental company doesn’t listen to the pod, TBD if Jenny knows the time for our next recording, Madi is her own task rabbit, and…
Jul 7, 2026 · 56:41
This week on The Player’s Box, we recap our live event last week where Madi had a food related meltdown, Des and Jenny had a sister moment in public and Jess nailed the hardest…
Jun 30, 2026 · 58:48
This week on The Player’s Box Jess and Des had an upsetting symphony behind them during Phantom of the Opera, Madi is going to handle the group dinner planning and the podcast…
Jun 23, 2026 · 43:04
This week on The Player’s Box we learn Jess’s other job for the pod, Madi’s passion for the Super Bowl, why the entire group chat turned on Des and whether Jenny is a good…
Jun 16, 2026 · 1:07:11
This week on The Player’s Box Jenny invites strangers into the bathroom, Madi’s legal at the DMV again but now has no air in her tires, Des comes to us mid-recording from the…
Jun 9, 2026 · 1:01:28
This week on The Player’s Box Jess is a brand rep for the Florida DMV while simultaneously the DMV seems to think Madi is a bot, if you see Jenny trying to break into your car…
Jun 2, 2026 · 1:01:07
This week on The Player’s Box Des and Jenny’s hypothetical celebrity dreams come true, headphones couldn’t save Jess from flying with the world’s most annoying couple and Madi…
May 26, 2026 · 1:09:11
This week on The Player’s Box we’re live from stage and a TV where we learn that Madi won’t even glamp (it’s still outdoors), Jenny was asked to not return to French class, don’t…
May 19, 2026 · 51:29
This week on The Player’s Box we learn everything not to do if you want to stay on the pod’s good side, including sending Jenny a voice memo with words, FaceTiming Jess, giving…
May 12, 2026 · 52:45
This week on The Player’s Box Des wants a ball gown-y dress, Jenny invents an incredible new phrase, Jess supports announcing an Irish goodbye, and nothing is coming between Madi…
May 5, 2026 · 1:02:07
This week on the Player’s Box Des has some Rome adventures for the ages, Madi’s alive and thriving with her nightly gelato, Jenny is back in the car remembering Iggy and an app…
Apr 28, 2026 · 1:00:39
This week on The Player’s Box the group decides Jess would be great on reality TV, Des accidentally broke into a stranger’s room, Madi’s back to slandering the wilderness and…
Apr 21, 2026 · 57:52
This week it's Jenny and Des vs. modes of transportation as Jenny is back to causing chaos in her car and Des had to sprint through an airport to rescue a lost item. Meanwhile,…
Apr 14, 2026 · 45:26
This week we put Jess, Jenny, Madi and Des in the hot seat and we see what secrets they’re willing to reveal. Jenny does not like what The Rock is cooking, Jess was dared to send…
Apr 7, 2026 · 1:02:05
This week on The Player's Box Des has our first ever live Unforced Error, Jess has a no bottoms moment (iykyk), someone in Europe is living with Jenny's identity and Madi…
Mar 31, 2026 · 57:42
This week we have a very special guest on The Player’s Box - Alex Eala! We also have a new host, Medison Cues, Jenny continues to catch lingering accusations, meanwhile Jess and…
Mar 24, 2026 · 52:46
This week on The Player’s Box Jenny basically moved into the Miami Open site, Jess brings us some gossip from the parking lot, Madi was signing body parts and Des accidentally…
Mar 17, 2026 · 45:59
This week on The Player’s Box Jenny used to love a Miami club, Madi agrees to willingly go for a run outside, Jess autographed her own wedding picture and Des is seconds away…
Mar 10, 2026 · 56:35
This week on The Player’s Box Jenny has a lot of superstitions specifically about towels, Madi almost missed a practice due to a sarcasm error, Des really wants you all to…
Mar 3, 2026 · 59:54
This week on The Player’s Box Madi is LIVID, Des hit Andy Roddick with a flag, Jess joined an 8pm recording at 7pm and Jenny is coming to us live from the back seat of a rental…
Feb 24, 2026 · 59:05
Today on The Player’s Box Jess is Miss Incredible, Madi was completely neglected by the entire podcast team, Des is still celebrating her birthday and Jenny had an unforced error…
Feb 17, 2026 · 1:04:33
Today we have a very special guest joining us in The Player’s Box — Iva Jovic! Jenny may be the new Quad God, Madi continues to be running’s biggest anti, Jess’s entire algorithm…
Feb 10, 2026 · 1:13:32
This week Des booked the same flight three times, Jess just wants a classic Marriott breakfast buffet and tensions rise as Jenny and Madi fight for their lives to describe girl…
Feb 3, 2026 · 1:03:37
This week is the moment you’ve all been waiting for as Madi takes a bite of Jess’s cheese pie. Does she love it? Hate it? Does her face go through 17 different emotions while…
Jan 27, 2026 · 56:56
This week we have some wild reveals like Jenny and Jess’s ideal high fashion sponsors (Ralph Lauren and Reese’s?), Des learns she may have broken Madi’s one player’s box rule and…
Jan 25, 2026 · 21:33
We’re releasing a special pre-match minisode this week to acknowledge the first ever Player’s Box on court match. Madi and Jess up the stakes with cheese pie (a potential…
Jan 20, 2026 · 1:08:03
This week Madi gives us an update from her time in Australia including her McDonald’s order, Jess attended a musical down under, Jenny is Vegemite’s biggest fan and Des gives us…
Jan 13, 2026 · 1:04:02
We learn a lot in this episode of The Player’s Box. In summary: Des would die in humidity, Jenny would win Naked and Afraid, Madi just wants to drink a spritz on the patio and…
Jan 6, 2026 · 1:03:22
Coco Gauff is our first-ever guest on The Player’s Box! Jess, Madi, Jenny and Des put their coolness to the test in a game of Coco or No-Go, they all play a game of Never Have I…
Dec 30, 2025 · 29:43
We’re off this week for New Years, but wanted to give you some Player’s Box to hold you over. Jess, Madi, Jenny and Des answer your fan questions. We’re back with regular…
Dec 23, 2025 · 35:20
We’re off this week for the holidays, but we wanted to make sure you had a little Player’s Box to hold you over. Jenny and Jess face Madi and Des in a trivia showdown and their…
Dec 16, 2025 · 54:49
This week Jess, Madi, Jenny and Des talk about their offseason training and schedules as they prepare for 2026. They vote on the first official Player’s Box Year End Awards,…
Dec 9, 2025 · 1:14:56
This week Jess, Madi, Jenny and Des catch us up on their Thanksgivings, their time in Buffalo and what it’s like to miss holidays due to their schedules. Then, they play a game…
Dec 2, 2025 · 1:01:49
This week we recorded before Thanksgiving so Jess, Madi, Jenny and Des discuss their plans, their favorite traditions and foods (who agrees with cheese on apple pie?). Then they…
Nov 25, 2025 · 1:00:48
This week Jess, Madi, Jenny and Des cover all of the major tennis headlines of the week. They then play a rapid fire game of most likely to - tennis edition. We end with a new…
Nov 18, 2025 · 56:11
This week Jess, Madi, Jenny and Des play a big game of what would you do — tennis edition. They also dive into why there tends to be coaching changes at the end of the year, and…
Nov 11, 2025 · 1:02:27
This week Madi, Jess, Jenny and Des come together for a big end of year wrap up. First they discuss the WTA Finals and Jess and Madi chat about their time in Riyadh. Then, they…
Nov 4, 2025 · 1:03:11
This week, Jess and Madi come to us from Riyadh and give us an update on all of the pre-event details including the behind-the-scenes of their photoshoot. Then, Des gives us an…
Oct 28, 2025 · 55:06
This week, Jess, Jenny, Madi and Des dive into Halloween stories and what they like (and don’t like) about this season. Then, they chat about recent gambling news that broke in…
Oct 21, 2025 · 57:28
This week everyone is back together as Des updates us on how things are going in Japan. They talk about their thoughts on the Six Kings Slam before jumping into fitness trends,…
Oct 14, 2025 · 52:49
Jess, Jenny and Madi are without Des this week due to navigating four different timezones. They dive into how to stay motivated towards the end of the year, anti-doping testing…
Oct 7, 2025 · 1:00:15
Join Jess and Des in China and Madi and Jenny in the States as they battle WiFi, lags and recording across the globe from each other. They cover recent tennis news, the WTA…
Sep 30, 2025 · 53:12
Jenny and Madi are on their own this week because Jess and Des couldn’t connect from Beijing. We learn more about where their friendship started and how it’s changed and…
Sep 23, 2025 · 1:03:29
On this week’s episode Jess, Madi, Jenny and Des kick things off with a new segment of Unforced Errors where they discuss what went wrong during their weeks. Then they go into…
Sep 16, 2025 · 46:23
Join Madi, Jess, Des and Jenny this week as they discuss the challenges of dating on the tour, all of their travel pet peeves as they prepare to head to China and then answer…
Sep 9, 2025 · 1:05:23
Join Jess, Madi, Jenny and Des as they do their final recap of their time at the US Open — including their peaks and pits, watching the semi-finals and all of the influencers and…
Sep 2, 2025 · 59:08
On this week’s episode of The Player’s Box, Jess, Madi, Des and Jenny recap their time so far at the US Open. Then, you get to know The Player’s Box with a round of most likely…
Aug 26, 2025 · 1:07:01
On the premiere episode of The Player’s Box, hosts Madison Keys, Jessica Pegula, Jennifer Brady and Desirae Krawczyk break down everything you should know heading into the US…
Aug 26, 2025 · 24:01
Madi, Jess, Jenny and Des take you from the group chat to the creation of the podcast — what made them finally launch one after years of talking about it? Plus, fan questions!…
Aug 24, 2025 · 2:14
Think you know your favorite athletes? You’ve seen them on the court, but what about the mishaps, late nights, and unexpected encounters that happen before the game starts? Step…
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