Stadium: Sir Vivian Richards Stadium
Referee: Michael Ragoonath
| Plunket Shield | 2017/02/15 17:25 | Trinidad & Tobago v Jamaica | 136/6,434/4 |
| Plunket Shield | 2019/11/24 13:00 | Jamaica v Leeward Islands | 255/8(50)-242/10(28.3) |
| Plunket Shield | 2019/11/22 17:30 | Combined Campuses & Colleges v Jamaica | 274/8(49.4)-272/10(49.4) |
| Plunket Shield | 2019/11/20 13:00 | Barbados v Jamaica | 305/8(50)-331/9(50) |
| Plunket Shield | 2019/11/18 13:00 | Jamaica v Canada | 244/9(50)-246/7(47.5) |
| Plunket Shield | 2019/11/16 17:30 | Jamaica v Canada | 243/6(50)-246/6(43.3) |
| Plunket Shield | 2019/11/12 17:30 | Combined Campuses & Colleges v Jamaica | 233/9(45.2)-330/8(50) |
| Plunket Shield | 2019/11/10 13:00 | Jamaica v Leeward Islands | 264/2(45.4)-262/9(50) |
| Plunket Shield | 2019/11/07 17:30 | Barbados v Jamaica | 265/10(50)-190/10(39.5) |
| Plunket Shield | 2019/11/29 17:30 | Trinidad & Tobago v Leeward Islands | 268/8(50)-269/6(49.3) |
| Plunket Shield | 2019/11/25 17:30 | West Indies Academy v Trinidad & Tobago | 79/0(18.3)-78/10(27.1) |
| Plunket Shield | 2019/11/23 17:30 | Guyana v Trinidad & Tobago | 220/4(44.3)-218/8(46) |
| Plunket Shield | 2019/11/21 17:30 | Trinidad & Tobago v USA | 177/3(41.5)-176/9(45) |
| Plunket Shield | 2019/11/17 17:30 | Trinidad & Tobago v Windward Islands | 179/10(28.3)-177/10(28.3) |
| Plunket Shield | 2019/11/15 17:30 | Trinidad & Tobago v USA | 244/4(30)-201/7(30) |
| Plunket Shield | 2019/11/13 17:30 | Trinidad & Tobago v West Indies Academy | 233/9(50)-243/10(50) |
| Plunket Shield | 2019/11/09 17:30 | Guyana v Trinidad & Tobago | 191/4(36)-187/9(43) |