How Cerundolo & Tiafoe Won Their Biggest-Ever Titles | Monday Match Analysis

It's the Wimbledon 2026 1st Round Show. We'll cover all of the following: Ben Shelton's gutting 5th-set tiebreak loss to Otto Virtanen, Serena Williams' comeback effort--- a loss to Maya Joint. Jannik Sinner found himself down 2-1, but survivied Miomir Kecmanovic. Novak Djokovic came through a high-quality battle with Yibing Wu, and more! 0:00 Intro 1:20 Virtanen d. Shelton 17:19 Joint d. Serena 29:49 Sinner d. Kecmanovic 36:10 Draper Withdrawal 38:10 Djokovic d. Wu 42:45 Mensik d. Samuel 46:12 Swiatek d. Townsend 47:52 Saffiulin d. Rublev IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On Monday Match Analysis, Gill Gross breaks down the 2026 Wimbledon men’s singles draw quarter-by-quarter, with dark horses, upset alerts, popcorn matchups and predictions. Top-seed Jannik Sinner is still hunting his first major title of the year. Alexander Zverev plays his first slam since getting his hands on an elusive trophy. Felix Auger-Aliassime and Ben Shelton round out the top seeds. 7-time Wimbledon champion Novak Djokovic, grass stalwart Taylor Fritz, the unpredictable Daniil Medvedev and young Jakub Mensik all enter with significant attention as well. 0:00 Intro 2:12 Sinner Q 13:15 Auger-Aliassime Q 21:44 Ben Shelton Q 30:45 Zverev Q 37:17 Final Weekend IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On Monday Match Analysis, Gill is joined by Alex Gruskin of Cracked Racquets to compare notes on their 2026 Wimbledon Power Rankings. In doing so, they discuss Jannik Sinner, Novak Djokovic, Alexander Zverev, Daniil Medvedev, Jack Draper, Alex De Minaur, Tommy Paul, Ben Shelton, Frances Tiafoe, Felix Auger-Aliassime, Joao Fonseca and others. 0:00 Intro 2:00 Honorable Mentions 5:30 10-9 26:20 8-7 40:30 6-5 48:30 4-3 54:35 2-1 IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Wimbledon champion Marketa Vondrousova has been handed a maximum 4-year ban for refusing a doping test. Gill Gross breaks down the case… IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On Monday Match Analysis, Gill Gross unpacks Francisco Cerundolo’s first ATP 500 title at the Queen’s Club after he beat Tommy Paul in three tight sets. Then, Frances Tiafoe joined the party with his biggest trophy, beating Taylor Fritz to take the title in Halle. 0:00 Intro 1:30 Grass Cerundolo 7:50 Nico Massu 11:15 Cerundolo def. Paul Analysis 28:23 Tiafoe def. Fritz Halle IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Gill Gross is joined by Sophie Amiach, author of recently released instructional tennis book, Tennis Smart & Simple (https://www.amazon.com/Tennis-Smart-Simple-Players-Coaches/dp/1950148009). We start with talk on Serena William's comeback, burning WTA Questions about Andreeva, Swiatek, Sabalenka, Gauff among others, and then get into your comments about tennis instruction. 0:00 Intro 1:00 Coached by BJK 5:40 Serena Comeback 13:10 WTA Burning Questions 23:40 Best Pro Model 29:00 Mid Match Adjustments 32:04 Sinner’s Forehand 37:05 JCF Comments 38:33 Matches vs. Drilling 43:40 Service Tosses 47:20 Two-Handed Forehands IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On Monday Match Analysis, Hall-of-Fame tennis writer Steve Flink joins the show as we wrap up coverage of Roland Garros 2026. We discuss the Major sea-change for Alexander Zverev, Jannik Sinner's physicality, the mid-2000s generation and my Disappointment Rankings. 0:00 Intro 1:15 Zverev’s Triumph 16:00 New 2 Era 18:00 Sinner’s Physicality 31:35 Slamless GOAT 34:30 Mid-200s Gen 44:06 Disappointment Rankings IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On the Mailbag, Gill Gross answers your comments post-Roland Garros 2026, including: now that they’re tied in slams who has had the better career between Alexander Zverev and Daniil Medvedev, how can Jannik Sinner fix his heat problem, which young players such as Mensik, Tien, Jodar and Fonseca are best built for grass, why isn’t Ben Shelton more consistent and much more. 0:00 Intro 1:30 Zverev vs Medvedev All-Time 7:05 Fixing Sinner’s Heat Issue 11:53 Top 10 Predictions 19:30 Zverev’s Future 23:40 Grass Questions 28:40 Zverev vs Wawrinka All-Time 33:00 Zverev l'équipe Interview 38:00 Cobolli and Chwalinska 41:50 Shelton Inconsistency 44:30 Sinner Press Conference 47:47 Stock Up Stock Down 51:50 Surface Homogenization 54:20 Wimbledon Seeding 56:20 Covering Zverev DV 57:55 Federer’s Athleticism 1:00:00 Media Boycott IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On Monday Match Analysis, Gill Gross breaks down Alexander Zverev's maiden major title at Roland Garros 2026. He beat Flavio Cobolli in 5-sets to finally shed the title of "the best to never win a slam." We'll cover what it means for his legacy, how he developed to get here, where he was better than Cobolli and how the final played out. Lastly, we'll hit on Zverev's controversial cloud off-court. 0:00 Intro 1:00 Legacy Changer 3:40 Zverev’s Development 9:50 Zverev d. Cobolli Keys 18:25 Chronological Analysis 38:35 DV Allegations IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

19-year old Mirra Andreeva battled qualifier Maja Chwalinska in the 2026 Roland Garros women's final. A first-time major champion was crowned. Gill Gross breakdown and analysis... IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.