Jamaica College Takes Home Another Trophy in a Year of Winning

Jamaica College added another title to its growing list of achievements in 2026 after the Jamaica College Old Boys Association of Florida defeated the Wolmer’s Old Boys Association of Florida 2 to 0 to win the Richard Davy Cup during True Blue Weekend 2026 in Miramar, Florida.

The match was part of the fourth staging of the invitational Richard Davy Cup and continued what has been a strong year for the Jamaica College community in sports and academics. Goals from Tevin Simpson and Ashani Walker secured the victory for Jamaica College, while Walker was named Man of the Match.

The result gave Jamaica College supporters another reason to celebrate after several major wins linked to the school during the year.

Another Win For The Jamaica College Community

The Richard Davy Cup victory took place during the 19th staging of True Blue Weekend, an annual event hosted by the Jamaica College Old Boys Association of Florida. The event brings together alumni, families, and supporters through entertainment and football activities in South Florida.

The football showdown between Jamaica College and Wolmer’s added another chapter to the rivalry between the schools. This year’s match ended with Jamaica College lifting the trophy once again in front of supporters gathered at Vizcaya Park in Miramar.

Ashani Walker played a key role in the win, scoring one of the goals and earning the Man of the Match award. Tevin Simpson also got on the scoresheet to help seal the 2 to 0 result.

The Richard Davy Cup was created in honor of former Jamaican football star Richard Davy, who attended both Jamaica College and Wolmer’s during his schoolboy football career.

A Strong Year In Schoolboy Sports

The latest trophy came during a year in which Jamaica College found success across several sporting competitions in Jamaica.

One of the biggest achievements came at the ISSA Boys and Girls Athletics Championships where Jamaica College reclaimed the Mortimer Geddes Trophy. The school finished with 345 points to secure the title and end the reign of their rivals.

Jamaica College also captured the All Island Under 14 Football Championship in 2026 and added another football title by becoming Under 16 football champions.

The success continued in table tennis where Jamaica College won both the Under 16 and Under 19 ISSA/JTACCUL All Island Championship titles. The Under 16 team secured their crown with a 5 to 0 win over Titchfield High School in the final.

These victories helped make 2026 one of the more successful years for Jamaica College sports in recent times.

Success Beyond Sports

The school’s achievements were not limited to athletics. Jamaica College also won the TVJ Schools’ Challenge Quiz competition in 2026. The victory marked the school’s first title in the competition in nearly 40 years.

The quiz title added another major accomplishment to a year that already included championships in football, athletics, and table tennis.

For many supporters and alumni, the combination of sporting and academic success reflected the strength of the Jamaica College community both in Jamaica and overseas.

True Blue Weekend Continues To Grow

True Blue Weekend itself also marked an important milestone in 2026 as the event celebrated its 19th anniversary in South Florida.

Organized by the Jamaica College Old Boys Association of Florida, the weekend included the Blue Magic kick off party and the annual SoccerFest competition. The event has become a gathering point for alumni and supporters living overseas while also supporting educational efforts connected to the school.

The weekend featured invitational matches, an alumni penalty kick competition, and recognition of Jamaican football figures who made an impact on schoolboy football over the years.

The Richard Davy Cup has now become one of the featured attractions of the weekend and continues to bring attention to the history and traditions tied to Jamaican schoolboy football.

Jamaica College Keeps Building Momentum

With victories in football, athletics, table tennis, and quiz competitions, Jamaica College supporters had many moments to celebrate throughout 2026. The Richard Davy Cup win in Florida added another trophy to the growing collection and showed how the school’s alumni network continues to carry the Jamaica College name beyond Jamaica.

For supporters, the latest victory was not just about one football match. It was another reminder of a year in which Jamaica College remained active and successful across several areas.