| Canada tour of West Indies | 1997/98 | - | |
| Red Stripe Bowl | 1997/98 | Leeward Is | |
| Bermuda tour of West Indies | 1999/00 | - | |
| Red Stripe Bowl | 1999/00 | Jamaica | |
| India A tour of West Indies | 1999/00 | - | |
| Cayman Islands tour of West Indies | 2000/01 | - | |
| Red Stripe Bowl (in West Indies) | 2000/01 | Windward Is | |
| Bermuda tour of West Indies | 2000/01 | - | |
| Red Stripe Bowl | 2001/02 | Guyana | |
| Canada tour of West Indies | 2002 | - | |
| Red Stripe Bowl | 2002 | Barbados | |
| Red Stripe Bowl (in West Indies) | 2003/04 | Guyana | |
| Regional Tournament (in West Indies) | 2004/05 | Trinidad & T | |
| KFC Cup (in West Indies) | 2005/06 | Guyana | |
| KFC Cup (in West Indies) | 2006/07 | Trinidad & T | |
| KFC Cup (in West Indies) | 2007/08 | Jamaica | |
| WICB Cup (in West Indies) | 2008/09 | Trinidad & T | |
| Canada tour of West Indies | 2008/09 | - | |
| President's Cup (West Indies) (in West Indies) | 2009/10 | Trinidad & T | |
| West Indies Cricket Board Cup | 2010/11 | shared | |
| Regional Super50 (in West Indies) | 2011/12 | Jamaica | |
| Regional Super50 (in West Indies) | 2012/13 | Windward Is | |
| Ireland tour of West Indies | 2013/14 | - | |
| Nagico Super50 (in West Indies) | 2013/14 | Barbados | |
| Nagico Super50 (in West Indies) | 2014/15 | Trinidad & T | |
| Nagico Super50 (in West Indies) | 2015/16 | Trinidad & T | |
| ICC Americas tour of West Indies | 2016/17 | - | |
| West Indies Cricket Board Regional Super50 | 2016/17 | Barbados | |
| Kent tour of West Indies | 2017/18 | - | |
| United States of America tour of West Indies | 2017/18 | - | |
| Super50 Cup (in West Indies) | 2017/18 | Windward Is | |
| Canada tour of West Indies | 2018/19 | - | |
| Super50 Cup (in West Indies) | 2018/19 | Comb C&C | |
| United States of America tour of West Indies | 2019/20 | - | |
| Super50 Cup (in West Indies) | 2019/20 | WI Emerging | |
| Super50 Cup (in West Indies) | 2020/21 | Trinidad & T | |
| Super50 Cup (in West Indies) | 2022/23 | Jamaica | |
| Super50 Cup (in West Indies) | 2023/24 | Trinidad & T | |