- April 30th - IMG Academy w/ Jimmy Arias & Miomir Kecmanović: How to Navigate in the Age of COVID-19
- May 4th - Current State of College Tennis & Looking Ahead with Tim Russell, CEO of Intercollegiate Tennis Association
- May 5th - Digging into the Business Side of Tennis with Todd Martin, CEO of International Tennis Hall of Fame, and Anne Worcester, Universal Tennis President
- May 7th - Transitions in Tennis with Claudio Pistolesi and Robin Soderling
- May 12 - Doubles: Learn to Cover the Net so you are Never Passed or Lobbed with Gigi Fernandez , Olympic Gold Medalist and 17x Grand Slam Doubles Champion
- May 13th - Junior Player Development with Brian Gottfried and Mal Washington
- Tuesday, May 5 - Rajeev Ram: The 2020 Australian Open doubles champion and Olympic Silver Medalist joins host Prakash Amritraj to dive into what makes a champion and how this top-20 doubles pro stays focused and fit.
- Thursday, May 7 - Shelby Rogers: Host Prakash Amritraj and Shelby Rogers (WTA #113) discuss her tennis journey and what it takes to perform at the highest level.
- May 12 - Darren Cahill: Host Prakash Amritraj goes “Inside the Coach’s Box” with the ESPN analyst and former coach of Andre Agassi, Lleyton Hewitt and Simona Halep.
- May 14 - Toni Nadal: Host Andre Sa goes “Inside the Coaches Box” with Toni Nadal. (En Espanol)
- May 19 - Danielle Collins & Mackenzie McDonald: The former college standouts and current pros join host Prakash Amritraj to discuss their transition from college to the pro tour.
- May 21 - Francis Roig & Jordi Vilaro: Host Andre Sa goes “Inside the Coach’s Box” with Rafa Nadal’s coach and the founders of Barcelona Total Tennis Academy. (En Espanol)
- May 28 - Andres Gomez: The former World No. 4 and 1990 French Open champion talks about his tennis journey with host Andre Sa. (En Espanol)