Stadium: Brian Lara Stadium
Referee: Michael Ragoonath Home Manager: David Williams Away Manager: Ian Allen
| Plunket Shield | 2019/11/07 17:30 | Trinidad & Tobago v Windward Islands | 239/2(42.5)-238/8(50) |
| Plunket Shield | 2018/10/17 18:00 | Windward Islands v Trinidad & Tobago | 78 All Out,83/3 |
| Plunket Shield | 2017/02/06 17:21 | Trinidad & Tobago v Windward Islands | 214 All Out,182/9 |