Post-Wimbledon Mega Mailbag (2025)

On Monday Match Analysis, Hall-of-Fame tennis writer Steve Flink joins the show as we wrap up coverage of Wimbledon 2025. We break down Jannik Sinner's sweet revenge over Carlos Alcaraz, Novak Djokovic's physical state, Taylor Fritz's standing amongst the best, Jack Draper's progress in spite of setback, dark press conferences for Alexander Zverev and Stefanos Tsitsipas, plus what we learned about Flavio Cobolli and Alexander Bublik in the last month plus. 0:00 Intro 0:45 Sinner & Alcaraz 20:37 Novak Djokovic 27:15 Taylor Fritz 30:52 Jack Draper 34:35 Alexander Zverev 39:00 Tsitsipas & Ivanisevic 43:46 Daniil Medvedev 49:35 Flavio Cobolli 51:37 Alexander Bublik IG: https://www.instagram.com/gillgross_/ TikTok: https://www.tiktok.com/@gill.gross 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join Evans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffee

On the post-Wimbledon 2025 Mega Mailbag, Gill Gross responds to your comments, including: who will win the Career Grand Slam first between Carlos Alcaraz and Jannik Sinner, is there any precedent of Grigor Dimitrov’s potentially history-altering injury, is Sinner already good enough to win Roland Garros next year, why is tennis discourse so tribalistic, why were there so many upsets at Wimbledon, what improvements did Iga Swiatek make to win Wimbledon, where does Sinner’s ballstriking rank all-time, is Darren Cahill going to retire, is Novak Djokovic going after Federer and Connors title records, are Jack Draper and Ben Shelton Sincaraz’s biggest threats, a Fabio Fognini retirement tribute, Nick Kyrgios’s analysis on Amanda Anisimova, Roddick’s take that Sinner slides too much, coverage of women’s tennis on the show, Agassi’s comments on Fritz’s return and more. 0:00 Intro 1:40 Career Grand Slam 5:11 Dimitrov’s Injury 10:50 Re-Analyzing RG Final 13:57 Tennis Tribalism Discourse 21:58 So Many Upsets 25:15 Swiatek Improvements 31:40 Sinner Ballstriking All-Time 34:30 Cahill Retirement 37:33 Djokovic Titles Count 40:49 Shelton & Draper Contendership 45:35 Djokovic Current Mental 49:55 SIncaraz Closeness 52:43 Fognini Tribute 57:02 Fritz or Zverev Slam 59:48 Sinner’s Last 52 Weeks 1:02:55 Kyrgios on Anisimova 1:05:05 Chasing Sincaraz Mentality 1:09:55 Sabalenka Slam Issues 1:12:40 Sincaraz H2H 1:15:40 Sinner Grass sliding 1:18:13 Learning From Losing 1:21:30 Women’s Coverage 1:24:20 Slow 2nd Serves 1:26:20 Agassi On Fritz 1:30:04 Sinner Emotion IG: https://www.instagram.com/gillgross_/ TikTok: https://www.tiktok.com/@gill.gross 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join Evans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffee

On Monday Match Analysis, Gill Gross breaks down Jannik Sinner's triumphant bounce back victory in the 2025 Wimbledon final against back-to-back-defending champion Carlos Alcaraz. We'll discuss all the things that Sinner improved and adjusted in order to win, as well as Alcaraz's biggest regrets, what we learned about the Italian and what it means for the rivalry moving forward. We're presented by Geau Sport Tennis Bags! Use the code Gill10 HERE: https://geausport.com/discount/Gill10 0:00 Intro 1:30 Sinner’s Pace 10:15 Sinner Improvements 28:40 Alcaraz Regrets 34:15 Sinner Mental 37:05 Sincaraz H2H IG: https://www.instagram.com/gillgross_/ TikTok: https://www.tiktok.com/@gill.gross 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join Evans Brothers Coffe Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffee

Iga Swiatek faced Amanda Anisimova in the Wimbledon 2025 Ladies Championships, both looking for their first title here. Gill Gross breakdown and analysis... IG: https://www.instagram.com/gillgross_/ TikTok: https://www.tiktok.com/@gill.gross 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join Evans Brothers Coffe Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffee

On Monday Match Analysis, Gill Gross breaks down Friday's semifinals and previews the men's championship at Wimbledon 2025. Jannik Sinner reached his first career Wimbledon final, exposing a limited Novak Djokovic, whose six-year streak of making the last Sunday is snapped. Carlos Alcaraz kept his chances for a 3rd straight Wimbledon title alive, taking out a focused Taylor Fritz. For a 7th straight slam, the champion will be Sinner or Alcaraz. 0:00 Intro 0:30 Sinner def. Djokovic 16:58 Alcaraz def. Fritz 26:12 Sinner-Alcaraz H2H 35:05 Sinner Keys 39:07 Alcaraz Keys 43:55 Prediction IG: https://www.instagram.com/gillgross_/ TikTok: https://www.tiktok.com/@gill.gross 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join Evans Brothers Coffe Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffee

On Monday Match Analysis, Gill Gross is joined by Giri Nathan to discuss the upcoming men's semifinals at Wimbledon 2025: Jannik Sinner vs. Novak Djokovic and Carlos Alcaraz vs. Taylor Fritz. We'll discuss what grass court looks like in the modern game, if this is Djokovic's last realistic chance to win his 25th major, how Sinner is an stylistic evolution of Djokovic, what we learned from their Roland Garros clash and why their head-to-head has recently turned towards the Italian. Then, we'll take on the recent dominance of Alcaraz over Sinner, Alcaraz's love affair with Wimbledon, and what Fritz might need to do in order to pull off the shocker. Pre-order Giri Nathan's upcoming book, CHANGEOVER, here: https://www.simonandschuster.com/books/Changeover/Giri-Nathan/9781668076248 0:00 Intro 1:00 Sinner vs. Shelton Analysis 11:00 Is Grass Too Slow 17:00 Djokovic’s Last Stand? 20:50 Sinner vs. Djokovic 40:41 Sincaraz H2H 48:20 Alcaraz vs. Fritz IG: https://www.instagram.com/gillgross_/ 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join

On Monday Match Analysis, Gill Gross starts by reacting to heartbreaking scenes at the end of the Jannik Sinner vs. Grigor Dimitrov match. Then, we dive into our four quarterfinal previews. Sinner will be hoping for a healthy elbow against Ben Shelton, Djokovic continues his quest against first-time quarterfinalist Flavio Cobolli, Taylor Fritz and Karen Khachanov clash in a meeting of similar styles and finally Carlos Alcaraz continues his three-peat quest against Cameron Norrie of Great Britain. We'll also discuss the 4th round efforts by Alex De Minaur and Andrey Rublev. We're presented by Geau Sport Tennis Bags! Use the code Gill10 HERE: https://geausport.com/discount/Gill10 0:00 Intro 0:55 Dimitrov vs. Sinner Reaction 10:15 Shelton Path 12:20 Sinner-Shelton H2H 15:30 Sinner-Shelton Prediction 21:28 Geau Sport 22:55 Cobolli Path 25:02 Djokovic Path 35:00 Djokovic-Cobolli H2H 35:37 Djokovic-Cobolli Prediction 38:25 Fritz Path 40:05 Khachanov Path 40:50 Fritz-Khachanov H2H 41:40 Fritz-Khachanov Prediction 43:33 Norrie Path 46:45 Alcaraz Path 48:30 Alcaraz-Norrie H2H 49:40 Alcaraz-Norrie Prediction IG: https://www.instagram.com/gillgross_/ 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join

On the Wimbledon 2025 3rd Round Show, Gill Gross starts with a reaction to Goran Ivanisevic's critical comments on Stefanos Tsitsipas following his first round retirement. Then we dive into matches such as Nicolas Jarry vs. Joao Fonseca, a form check on title favorites Novak Djokovic, Jannik Sinner and Carlos Alcaraz, the blockbuster night match between Aryna Sabalenka and Emma Raducanu, Laura Siegemund's stunner over Madison Keys, Taylor Fritz vs. Alejandro Davidovich Fokina, Flavio Cobolli's impressive display against Jakub Mensik and more. 0:00 Intro 1:00 Ivanisevic on Tsitsipas 11:20 Jarry d. Fonseca 22:13 Djokovic, Sinner, Alcaraz 32:10 Sabalenka d. Raducanu 39:40 Siegemund d. Keys 43:20 Fritz d. ADF 45:20 Cobolli d. Mensik 51:05 Khachanov d. Borges 53:18 Shelton d. Fucsovics 56:48 Sonego d. Nakashima 59:30 1st-Time Champion IG: https://www.instagram.com/gillgross_/ 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join

On the Wimbledon 2025 3rd Round Show, Gill Gross starts with a breakdown of Marin Cilic's vintage performance to oust 4-seed Jack Draper. Then, we'll go through the men's draw and update predictions. We'll talk Taylor Fritz's return strategy after he conquered yet another huge server in Gabriel Diallo. Other topics include Joao Fonseca's quick grass learning, Novak Djokovic's A-PLUS performance against Dan Evans, Cam Norrie's upset over Frances Tiafoe and why Gill is still high on Jakub Mensik. We're presented by Geau Sport Tennis Bags! Use the code Gill10 HERE: https://geausport.com/discount/Gill10 0:00 Intro 0:45 Cilic d. Draper 20:21 Predictions Update 28:45 Fritz d. Diallo 43:00 Fonseca Through 45:38 Norrie d. Tiafoe 49:30 Alcaraz d. Tarvet 49:54 Struff d. FAA 52:00 Mensik d. Giron 53:39 Djokovic Masterclass 58:09 Jaume Munar 59:00 Swiatek d. McNally 59:48 Ofner d. Paul IG: https://www.instagram.com/gillgross_/ 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join

On the 2025 Wimbledon 1st Round Mailbag, Gill Gross answers your questions about one of the most chaotic opening two days in tournament history. We’ll talk 90’s generation decline, Carlos Alcaraz’s surprise 5-setter against Fabio Fognini, Daniil Medvedev upset defeat against Benjamin Bonzi, Holger Rune’s blown lead against Nicolas Jarry, Jannik Sinner’s firing of his physical team, a comprehensive upset surprise meter, Stefanos Tsitsipas’s retirement due to a back injury, how the heat got to Berrettini and Musetti, the epic 5-set showdown between Taylor Frtiz and Giovanni Mpetshi Perricard, Coco Gauff’s disappointing showing versus Dayana Yastremska, another opening round win for Joao Fonseca and Alexander Bublik’s Wimbledon letdown against an impressive Jaume Munar. 0:00 Intro 1:50 90’s Gen Decline 7:10 Alcaraz d. Fognini 12:08 Medvedev Upset 21:55 Rune Upset 33:37 Sinner Fires Physio 36:36 Upset Surprise Meter 43:20 Tsitsipas Retirement 52:35 Rapid Fire 1:02:12 Berrettini & Musetti 1:05:58 Fritz d. Perricard 1:17:26 Gauff Upset 1:21:30 Fonseca d. Fearnley 1:23:36 Bublik Upset IG: https://www.instagram.com/gillgross_/ 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join