The 2005 Caribbean Cup (known as the Digicel Caribbean Cup for sponsorship reasons) was the thirteenth edition of the Caribbean Cup hosted by Barbados and won by Jamaica. In all, 30 countries were invited, of which, 22 participated and 8 withdrew.
Qualifying tournament
First qualifying round (group stage)
Group A
Group A Qualifier: Saint-Martin w/o (Sint Maarten withdrew)
Played in Kingston, Jamaica
Group B
Played in Martinique
Group C
Group C qualifier: withdrew.
Bahamas qualified but they also withdrew; their place was taken by Guyana. The participants were supposed to be: , , , , and the matches were planned to be played in Cuba. However, Netherlands Antilles, Guyana, Dominican Republic all withdrew later, and so Cuba won the group automatically.
Group D
Group D qualifier: both through . The matches were scheduled to be played on 5 and 11 September but Guyana were requested to replace the Bahamas from Group C who withdrew so Suriname was drawn into Group D.
Played in Trinidad and Tobago
Group E
Group E qualifier: w/o (Aruba withdrew)
Played in Saint Vincent; originally planned for Cayman Islands, but rescheduled due to hurricane damage
NB: Bermuda have protested the eligibility of three BVI players (Montgomery Butler, Avondale Williams, Venton James) as being Saint Vincentians.
Group F
Group F qualifier: w/o (Anguilla withdrew)