RESTAURANTS AND BARS
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Join us for the Rosewood Little Dix Bay Cup, where you'll have the rare opportunity to connect with tennis legends Madison Keys and Jennifer Brady, alongside fellow enthusiasts from around the world. Set against the stunning backdrop of our resort’s courts, this exclusive tournament, taking place December 4-6, 2026, promises an unforgettable blend of world-class competition and luxury hospitality.
Madison Keys
Player
Madison Keys is an American professional tennis player known for her powerful serve, aggressive baseline game, and composed presence on court. A Grand Slam champion and top-ranked WTA competitor, Keys has become one of the sport’s most respected players, celebrated for her resilience, athleticism, and inspiring journey at the highest level of tennis.
Jennifer Brady
Player
Jennifer Brady is an American professional tennis player known for her powerful serve, athletic baseline game, and determined competitive spirit. A former World No. 13, Brady reached the final of the 2021 Australian Open and the semifinals of the 2020 US Open, establishing herself as one of the leading American players of her generation.
Chris Eubanks
Event Emcee
Christopher “Chris” Eubanks is a retired American professional tennis player known for his towering serve, effortless athleticism, and charismatic presence on and off the court. A former World No. 29, Eubanks captured his first ATP title at the 2023 Mallorca Championships and reached the Wimbledon quarterfinals that same year, marking the standout run of his career.
Welcome Dinner
Friday Evening
Mingle with fellow guests and world-class tennis pros while savoring fine wines and a curated selection of local culinary delights. The evening continues with a dinner inspired by our exclusive Chef’s Table experience, featuring signature dishes crafted with the vibrant flavors of the BVI. Conclude the night with an intimate Q&A session with tennis stars Madison Keys, Jennifer Brady, and Chris Eubanks.
Champions’ Clinic
Saturday Morning
Step onto the court with tennis champions Madison Keys and Jennifer Brady for an exclusive, hands-on clinic. Learn from their expertise as they share insider techniques, strategic insights, and personal tips to elevate your game.
Exhibition Match
Saturday Afternoon
Enjoy a thrilling exhibition match featuring tennis legends Madison Keys and Jennifer Brady, with event emcee Chris Eubanks. Witness elite athleticism, courtside camaraderie, and the electrifying passion and power these champions bring to the game. Drinks and light bites to be served during the match.
Community Experience
Sunday Morning
A group of children from the local community are invited to Rosewood Little Dix Bay for a special opportunity to learn and play alongside Madison and Jennifer. During this exclusive clinic, the young participants will be guided through the fundamentals of the game in a fun, inspiring, and encouraging environment.