| Date | R | Home v Away | - |
|---|---|---|---|
| 11/27 13:00 | - | Trinidad & Tobago v Leeward Islands | 214/2(43.1)-213/10(49) |
| 11/25 13:00 | - | Leeward Islands v Guyana | Cancelled |
| 11/23 13:00 | - | Leeward Islands v Jamaica | View |
| 11/21 13:00 | - | Leeward Islands v Barbados | 138/10(25.1)-139/3(23.3) |
| 11/19 18:00 | - | Leeward Islands v Windward Islands | 324/10(47.3)-325/8(43.5) |
| 11/21 17:00 | 2 | Jamaica v Leeward Islands | 352/9(50)-245/10(34.4) |
| 11/17 13:00 | - | Combined Campuses & Colleges v Leeward Islands | 151/10(36)-154/6(19.4) |
| 11/15 17:00 | - | Leeward Islands v Jamaica | 182/10(34.3)-264/9(43) |
| 11/08 13:00 | - | Leeward Islands v Windward Islands | 180/10(48.4)-96/10(21) |
| 11/05 17:00 | - | Leeward Islands v Guyana | 139/10(34.2)-141/2(27.5) |
| 11/03 17:00 | - | Trinidad & Tobago v Leeward Islands | 291/6(50)-292/3(47.3) |
| 11/01 13:00 | - | Barbados v Leeward Islands | 285/7(49.4)-284/5(50) |
| 10/30 13:00 | - | West Indies Academy v Leeward Islands | 94/10(27.5)-236/7(47) |
| 11/11 17:00 | 1 | Trinidad & Tobago v Leeward Islands | 141/3(23.4)-135/10(41.5) |
| 11/09 17:00 | 2 | Leeward Islands v Barbados | 290/10(49.4)-135/10(30.2) |
| 11/04 13:00 | - | Combined Campuses & Colleges v Leeward Islands | Cancelled |
| 11/02 17:00 | - | Leeward Islands v Barbados | 192-196 |
| 10/31 13:00 | - | Windward Islands v Leeward Islands | 179-293 |
| 10/26 17:00 | - | Trinidad & Tobago v Leeward Islands | 199-198 |
| 10/23 13:00 | - | Guyana v Leeward Islands | 248/6(47.3)-244/6(50) |
| 10/21 13:00 | - | Leeward Islands v West Indies Academy | 239/10(48.5)-173/10(40) |
| 10/18 17:00 | - | Leeward Islands v Jamaica | 124/2(14)-123/10(32.5) |
| 11/13 18:00 | - | Barbados v Leeward Islands | 271/5(47)-273/7(50) |
| 11/11 13:00 | - | Jamaica v Leeward Islands | 182/6(36.5)-207/10(48.5) |
| 11/09 18:00 | - | Leeward Islands v West Indies Emerging Team | 213/6(46.1)-211/10(47.2) |
| 11/06 18:00 | - | Barbados v Leeward Islands | ,243/8 |
| 11/01 17:00 | - | Leeward Islands v Jamaica | 270/9(50)-202/9(50) |
| 10/29 17:00 | - | Leeward Islands v West Indies Emerging Team | 191/7(39)-190/9(50) |
| 02/26 13:00 | 31 | Barbados v Leeward Islands | 265-270 |
| 02/19 13:00 | - | Leeward Islands v Jamaica | 187-220 |