| Red Stripe Bowl, 1997/98 | 1997/98 | Leeward Is | |
| Commonwealth Games (in Malaysia), 1998/99 | 1998/99 | South Africa | |
| Red Stripe Bowl, 1999/00 | 1999/00 | Jamaica | |
| Red Stripe Bowl (in West Indies), 2000/01 | 2000/01 | Windward Is | |
| Red Stripe Bowl, 2001/02 | 2001/02 | Guyana | |
| Red Stripe Bowl, 2002 | 2002 | Barbados | |
| Red Stripe Bowl (in West Indies), 2003/04 | 2003/04 | Guyana | |
| Regional Tournament (in West Indies), 2004/05 | 2004/05 | Trinidad & T | |
| KFC Cup (in West Indies), 2005/06 | 2005/06 | Guyana | |
| KFC Cup (in West Indies), 2006/07 | 2006/07 | Trinidad & T | |
| KFC Cup (in West Indies), 2007/08 | 2007/08 | Jamaica | |
| WICB Cup (in West Indies), 2008/09 | 2008/09 | Trinidad & T | |
| President's Cup (West Indies) (in West Indies), 2009/10 | 2009/10 | Trinidad & T | |
| West Indies Cricket Board Cup, 2010/11 | 2010/11 | shared | |
| Regional Super50 (in West Indies), 2011/12 | 2011/12 | Jamaica | |
| Regional Super50 (in West Indies), 2012/13 | 2012/13 | Windward Is | |
| Nagico Super50 (in West Indies), 2013/14 | 2013/14 | Barbados | |
| Nagico Super50 (in West Indies), 2014/15 | 2014/15 | Trinidad & T | |
| Nagico Super50 (in West Indies), 2015/16 | 2015/16 | Trinidad & T | |
| West Indies Cricket Board Regional Super50, 2016/17 | 2016/17 | Barbados | |
| Super50 Cup (in West Indies), 2017/18 | 2017/18 | Windward Is | |
| Super50 Cup (in West Indies), 2018/19 | 2018/19 | Comb C&C | |
| Super50 Cup (in West Indies), 2019/20 | 2019/20 | WI Emerging | |
| Super50 Cup (in West Indies), 2020/21 | 2020/21 | Trinidad & T | |
| Super50 Cup (in West Indies), 2022/23 | 2022/23 | Jamaica | |
| Super50 Cup (in West Indies), 2023/24 | 2023/24 | Trinidad & T | |
| Super50 Cup (in West Indies), 2024/25 | 2024/25 | - | |
| Super50 Cup (in West Indies), 2025/26 | 2025/26 | Barbados | |