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Courtside Elegance, Caribbean Spirit

3rd Annual Round Hill Tennis Cup

3 Nights | 4 Days | 4 Tennis Pros | Elite Pro-Am Experience

November 4 (Wednesday) to November 7 (Saturday), 2026

The Round Hill Tennis Cup is our premier multi day celebration of world class tennis, Caribbean elegance, and vibrant camaraderie. This exclusive event unites passionate amateur players with elite professional athletes for an unforgettable weekend of competition and connection on our lush, ocean view courts.

Designed for players of all skill levels, the experience pairs guests directly with top tier talent for a dynamic, highly social tournament format. Beyond the competitive thrill, it is a gathering centered around the joy of the game, beautiful connections, and unforgettable island memories.

From intensive masterclasses to high energy exhibition matches, every moment builds toward our grand weekend finale, celebrating the perfect harmony of exceptional sport and sophisticated island living.

Reserve your tennis experience

The Round Hill Tennis Cup Experience

Join us for an unforgettable tennis experience at Round Hill with world-class instruction and exclusive on-court access.

Full Event Registration – $995 + taxes per guest
Includes complete participation in all Cup events, tournament play, evening receptions, and the exclusive Pro-Am tournament.

Masterclass Pass – $250 + taxes per session
Enjoy access to an individual Morning Masterclass Clinic with one of our four featured tennis professionals. (Does not include Pro-Am Tournament eligibility.)

Playing spots are strictly limited to ensure an intimate experience, personalized instruction, and maximum court time with Nicolás Almagro and our featured pros.

The Schedule of Events

Thursday, November 5 | 4:45 PM - 5:45 PM

Professional Tennis Exhibition

Experience courtside thrills as our pros take the court for an explosive live exhibition match. Witness the incredible power, speed, and tactical brilliance of world class tennis up close, set against the breathtaking tropical backdrop of our estate. Complimentary refreshments will be served.

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Featured Pros

A Retrospective of Our Past Cups

Our tradition of excellence continues. When you join the Round Hill Tennis Cup, you step into a legacy that has consistently welcomed the world's finest tennis talent to our tropical courts.

Some of our past featured professionals:

Kevin Anderson

Former World No. 5, two-time Grand Slam Finalist at the US Open and Wimbledon, and winner of 7 ATP singles titles

Marcelo Arévalo

Former world No. 1 in Men's Doubles by the ATP, 2 Time French Open Doubles Winner, and 16 Career doubles titles

Shelby Rogers

Former world No. 30 Women's singles player

Bianca Andrescu

Former world No. 4 in Women's singles, and 2019 US Open singles Champion

Tommy Robredo

Former World No. 5, winner of 11 ATP singles titles, and legendary Spanish clay court master

Dominik Hrbatý

Former World No. 12, French Open semi-finalist, and Davis Cup finalist

Contact Us

The Schedule of Events

Featured Pros

A Retrospective of Our Past Cups

Login to get access and download the images

Contact Us

The Schedule of Events

Featured Pros

A Retrospective of Our Past Cups

Stay in Touch

Login to get access and download the images