| Red Stripe Bowl, 1997/98 | 1997/98 | Leeward Is | |
| Busta Cup (in West Indies), 1999/00 | 1999/00 | Jamaica | |
| Busta Cup (in West Indies), 2000/01 | 2000/01 | Jamaica | |
| Red Stripe Bowl, 2001/02 | 2001/02 | Guyana | |
| Busta Cup, 2001/02 | 2001/02 | Jamaica | |
| Red Stripe Bowl, 2002 | 2002 | Barbados | |
| Carib Beer Cup, 2002/03 | 2002/03 | Barbados | |
| Red Stripe Bowl (in West Indies), 2003/04 | 2003/04 | Guyana | |
| Carib Beer Cup (in West Indies), 2003/04 | 2003/04 | Barbados | |
| Regional Tournament (in West Indies), 2004/05 | 2004/05 | Trinidad & T | |
| Carib Beer Cup (in West Indies), 2004/05 | 2004/05 | Jamaica | |
| KFC Cup (in West Indies), 2005/06 | 2005/06 | Guyana | |
| Carib Beer Cup (in West Indies), 2005/06 | 2005/06 | Windward Is | |
| Carib Beer Challenge (in West Indies), 2005/06 | 2005/06 | Trinidad & T | |
| Carib Beer Series (in West Indies), 2006/07 | 2006/07 | Barbados | |
| KFC Cup (in West Indies), 2006/07 | 2006/07 | Trinidad & T | |
| Carib Beer Series (in West Indies), 2007/08 | 2007/08 | Jamaica | |
| Regional Four Day Competition (in West Indies), 2008/09 | 2008/09 | Jamaica | |
| President's Cup (West Indies) (in West Indies), 2009/10 | 2009/10 | Trinidad & T | |
| Regional Four Day Competition (in West Indies), 2009/10 | 2009/10 | Jamaica | |
| Caribbean T20 (in West Indies), 2010 | 2010 | Guyana | |
| West Indies Cricket Board Cup, 2010/11 | 2010/11 | shared | |
| Regional Four Day Competition (in West Indies), 2010/11 | 2010/11 | Jamaica | |
| Regional Super50 (in West Indies), 2011/12 | 2011/12 | Jamaica | |
| Regional Four Day Competition (in West Indies), 2011/12 | 2011/12 | Jamaica | |
| Caribbean T20 (in West Indies), 2012/13 | 2012/13 | Trinidad & T | |
| Regional Four Day Competition (in West Indies), 2012/13 | 2012/13 | Barbados | |
| Regional Super50 (in West Indies), 2012/13 | 2012/13 | Windward Is | |
| Nagico Super50 (in West Indies), 2013/14 | 2013/14 | Barbados | |
| Regional Four Day Competition (in West Indies), 2013/14 | 2013/14 | Barbados | |
| Nagico Super50 (in West Indies), 2014/15 | 2014/15 | Trinidad & T | |
| WICB Professional Cricket League Regional 4 Day Tournament (in West Indies), 2014/15 | 2014/15 | Guyana | |
| WICB Professional Cricket League Regional 4 Day Tournament (in West Indies), 2015/16 | 2015/16 | Guyana | |
| West Indies Cricket Board Regional Super50, 2016/17 | 2016/17 | Barbados | |
| WICB Professional Cricket League Regional 4 Day Tournament (in West Indies), 2016/17 | 2016/17 | Guyana | |
| WICB Professional Cricket League Regional 4 Day Tournament (in West Indies), 2017/18 | 2017/18 | Guyana | |
| WICB Professional Cricket League Regional 4 Day Tournament (in West Indies), 2018/19 | 2018/19 | Guyana | |
| West Indies Championship, 2019/20 | 2019/20 | Barbados | |
| Super50 Cup (in West Indies), 2020/21 | 2020/21 | Trinidad & T | |
| West Indies 4-Day Championship, 2021/22-2022 | 2021/22-2022 | Barbados | |
| West Indies Championship, 2022/23 | 2022/23 | Guyana | |
| Super50 Cup (in West Indies), 2023/24 | 2023/24 | Trinidad & T | |
| West Indies Championship, 2023/24 | 2023/24 | Guyana | |
| Super50 Cup (in West Indies), 2024/25 | 2024/25 | - | |
| West Indies Championship, 2024/25 | 2024/25 | Guyana | |