DAY 1 – OPENING EXHIBITION MATCH
Thursday, November 13, 2025
​3:30 PM – EXHIBITION MATCH: TEAM HOWARD VS. JAMAICA ALL STARS TEAM
A showcase of national pride and rising talent. This exhibition pits Team Howard against Jamaica's top talent including Blaise Bicknell in a spirited, fan-friendly format that highlights the heart of the Jamaica Cup—connection, culture, and competition.
Includes courtside seating for VIP guests and sponsors.
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DAY 2 – EXHIBITION SHOWDOWN: PROS VS. TEAMS
Friday, November 14, 2025
Location: Half Moon Tennis Courts, Montego Bay
​3:30 PM – EXHIBITION MATCH: TEAM HOWARD OR JAMAICA ALL STARS VS. ATP & WTA PROS
In this special crossover exhibition, ATP and WTA stars will face off against either Team Howard or Jamaica All Stars in a dynamic team format. Expect fierce rallies, entertaining moments, and matchups unique to the Jamaica Cup!
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FOLLOWED BY: PRO EXHIBITION MATCH - MIXED DOUBLES
Enjoy an exclusive courtside experience as four of our featured pros — Lauren Davis, Jenson Brooksby, Blaise Bicknell, and Christina McHale — team up for a dynamic mixed doubles exhibition. A highlight of the Jamaica Cup weekend, this friendly competition delivers unforgettable moments both on and off the court.
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Includes courtside seating for VIP guests and sponsors.
DAY 3 – FEATURED WTA & ATP EXHIBITION MATCHES
Saturday, November 15, 2025
Location: Half Moon Tennis Courts, Montego Bay
3:30 PM – WTA EXHIBITION MATCH
Christina McHale vs. Lauren Davis
A former World No. 24 and U.S. Olympian, Christina McHale returns to the spotlight in a showcase match against Lauren Davis, former World No. 26.
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FOLLOWED BY – ATP EXHIBITION MATCH
Jenson Brooksby vs. Blaise Bicknell
In a true Jamaica Cup highlight, American ATP star Jenson Brooksby takes on Jamaican standout Blaise Bicknell in a high-stakes exhibition.
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Includes courtside seating for VIP guests and sponsors.
DAY 4 – JAMAICA CUP PRO-AM & VIP PLAYERS’ PARTY
Sunday, November 16, 2025
10:30 AM – JAMAICA CUP PRO-AM
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Join us at the Pro-Am, often viewed as the highlight of the Jamaica Cup, where VIP guests and sponsors take the court alongside WTA & ATP pros in a fun yet competitive format. This exclusive experience offers an up-close connection with the athletes. Light refreshments and hospitality for players and guests is included. Only 25 spots available!
5:00 PM – VIP PLAYERS’ PARTY
An exclusive, invitation-only evening hosted by Half Moon with all Jamaica Cup pro players in attendance, set against the backdrop of an elegant Caribbean escape. This unforgettable closing celebration features:
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Rounds of appetizers and drinks
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Island-inspired ambiance
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Player meet-and-greets and premium photo opportunities
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An intimate experience alongside the athletes
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A celebratory finale with select guests, media, and sponsors
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Please note: This event is hosted by Half Moon and for registered hotel guests only
​ Schedule is tentative and subject to change any time prior to or during the event.