| Shell Shield | |
| 1965/66 | Barbados |
| 1966/67 | Barbados |
| 1967/68 | No competition |
| 1968/69 | Jamaica |
| 1969/70 | Trinidad and Tobago |
| 1970/71 | Trinidad and Tobago |
| 1971/72 | Barbados |
| 1972/73 | Guyana |
| 1973/74 | Barbados |
| 1974/75 | Guyana |
| 1975/76 | Barbados |
| Trinidad and Tobago | |
| 1976/77 | Barbados |
| 1977/78 | Barbados |
| 1978/79 | Barbados |
| 1979/80 | Barbados |
| 1980/81 | Combined Islands |
| 1981/82 | Barbados |
| 1982/83 | Guyana |
| 1983/84 | Barbados |
| 1984/85 | Trinidad and Tobago |
| 1985/86 | Barbados |
| 1986/87 | Guyana |
| Red Stripe Cup | |
| 1987/88 | Jamaica |
| 1988/89 | Jamaica |
| 1989/90 | Leeward Islands |
| 1990/91 | Barbados |
| 1991/92 | Jamaica |
| 1992/93 | Guyana |
| 1993/94 | Leeward Islands |
| 1994/95 | Barbados |
| 1995/96 | Leeward Islands |
| 1996/97 | Barbados |
| President’s Cup | |
| 1997/98 | Guyana |
| Leeward Islands | |
| Busta Cup | |
| 1998/99 | Barbados |
| 1999/00 | Jamaica |
| 2000/01 | Barbados |
| 2001/02 | Jamaica |
| Carib Beer Cup | |
| 2002/03 | Barbados |
| 2003/04 | Barbados |
| 2004/05 | Jamaica |
| 2005/06 | Trinidad and Tobago |
| 2006/07 | Barbados |
| 2007/08 | Jamaica |
| Regional 4 Day Competition | |
| 2008/09 | Jamaica |
| 2009/10 | Jamaica |
| 2010/11 | Jamaica |
| 2011/12 | Jamaica |
| 2012/13 | Barbados |
| 2013/14 | Barbados |
| Headley-Weekes Trophy | |
| 2013/14 | Jamaica |
| WICB Professional Cricket League | |
| 2014/15 | Guyana |
| 2015/16 | Guyana |
| 2016/17 | Guyana |
| 2017/18 | Guyana |
| 2018/19 | Guyana |
| 2019/20 | Barbados |
| 2020/21 | No competition due to Covid-19 |
| West Indies Championship | |
| 2021/22 | Barbados |
| 2022/23 | Guyana |
| 2023/24 | Guyana |
Denis Moore