On 28 Sept., the Cayman Islands Football Association’s 2025/26 domestic football season will kick off with two Charity Shield matches.
CIFA’s Women’s League champions Sunset FC will take on league runners-up Scholars ISC in the first match, kicking off at 5pm at the Truman Bodden Sports Complex.
Following the women’s match, the men’s Charity Shield is set to begin at 7:30pm, featuring a showdown between Elite SC, the reigning CIFA Premier League champions, and FA Cup winners Tigers.
Last year’s Charity Shield saw Scholars ISC men win their match 3-1 against Academy, while in the women’s fixture, Sunset FC was victorious over Elite SC with a 3-0 score.
“This is an exciting time,” CIFA President Alfredo Whittaker said in a press release.

“The start of a new season brings with it a renewed sense of pride and determination as clubs and players begin the journey to reach their goals. We wish all clubs the best of luck this season,” he added.
Beyond the competition, the Charity Shield will once again serve as a fundraiser for a local non-profit.
This year, CIFA will match all gate proceeds and donate the total to Feed Our Future, an organisation dedicated to solving childhood hunger in the Cayman Islands.
Last year, the association donated $2,280 to Sustainable Cayman, which promotes environmental sustainability and conservation across the islands.







