Caribbean Cup
The Caribbean Cup was the championship tournament for national association football teams that are members of the Caribbean Football Union. The first competition, established by Shell and run by former England Cricket fast bowler Fred Rumsey, was contested in 1989 in Barbados. The Caribbean Cup served as a qualification tournament among CFU members for the CONCACAF Gold Cup. The Caribbean Cup replaced the CFU Championship competition which was active between 1978 and 1988.
Trinidad and Tobago, eight-time winners, and Jamaica, six-time winners, were the most successful sides, winning a combined 14 of 18 titles. Martinique, Haiti, Cuba and Curaçao also won the tournament.
In 1990 on the day of the final, an insurrection in Trinidad and Tobago, the host nation, by the Jamaat al Muslimeen forced an abandonment of the tournament with only the final and 3rd place play-off game remaining. Also, the tournament was not held in 2000, 2002 and 2003.
The 2017 edition of the tournament was the 19th and final. The tournament was discontinued in favor of participation in the CONCACAF Nations League.
Sponsors
Over the years, the tournament has been named after its respective sponsors. Shell had sponsored the competition since its inception in 1989.By February 1996, Jack Warner had announced a new sponsorship from sports apparel company Umbro for the 1996 Caribbean Cup. The tournament was also co-sponsored by Umbro in 1997 before Shell re-attained sole-sponsorship for the 1998 event.
In October 1998, during the first and only year of sponsorship from the Asia Sport Group, the competition changed its name to Copa Caribe. CFU's chairman Jack Warner stated that the change was made to highlight the competition being a branch of the Copa de Oro. Florida-based Inter/Forever agreed a sponsorship deal to replace the Asia Sport Group agreement in January 1999. The competition retained the title Copa Caribe for the 1999 and 2001 editions.
There was no competition held in 2003, instead teams focused on a group-stage only qualifying tournament.
Caribbean-based mobile phone company Digicel took over the sponsorship in 2004, in June 2007 they agreed to sponsor the 2008 and 2010 events. The 2012 and 2014 editions of the competition had no title sponsor, while the last tournament was sponsored by Scotiabank.
Tournaments
Cumulative results
The following is a compiled national level championship table for the CFU region. Years in italics indicate that a nation was the host or co-host.| Team | Titles | Runners-up | Third place | Fourth place |
| 8 | 5 | 2 | 0 | |
| 6 | 3 | 2 | 0 | |
| 1 | 3 | 3 | 4 | |
| 1 | 1 | 4 | 0 | |
| 1 | 1 | 3 | 2 | |
| 1 | 0 | 0 | 1 | |
| 0 | 2 | 0 | 2 | |
| 0 | 1 | 3,, | 1 | |
| 0 | 1 | 0 | 1 | |
| 0 | 1 | 0 | 0 | |
| 0 | 0 | 1 | 0 | |
| 0 | 0 | 1 | 0 | |
| 0 | 0 | 0 | 2 | |
| 0 | 0 | 0 | 1 | |
| 0 | 0 | 0 | 1 | |
| 0 | 0 | 0 | 1 | |
| 0 | 0 | 0 | 1 |
Awards
| Year | Most Valuable player | Top Goalscorer | Best goalkeeper | Fair play award |
| 1989 |  Steve Mark |  Dwight Yorke, Philbert Jones | ||
| 1991 |  Paul Davis | Paul Davis | ||
| 1992 |  Leonson Lewis | |||
| 1993 | Walter Boyd |  Jean-Michel Modestin | ||
| 1994 | David Nakhid | |||
| 1995 | David Nakhid | |||
| 1996 | Russell Latapy | |||
| 1997 | Jerren Nixon | Clayton Ince | ||
| 1998 | Stern John | Stern John | Clayton Ince | |
| 1999 |  Raciel Martínez | Ariel Álvarez | Clayton Ince | |
| 2001 | Dennis Lawrence |  Golman Pierre | Clayton Ince | |
| 2005 | Andy Williams | Luton Shelton | ||
| 2007 | Pierre Richard Bruny | Gary Glasgow | ||
| 2008 | Eric Vernan | Kithson Bain, Luton Shelton | ||
| 2010 | Rodolph Austin | Dane Richards, Kithson Bain | ||
| 2012 | eight players | |||
| 2014 | Rodolph Austin |  Kervens Belfort,  Darren Mattocks and  Kevin Molino | Andre Blake | |
| 2017 |  Gino van Kessel | Elson Hooi |