| 374-6 | Windward Islands v Barbados | Shaw Park, Scarborough | 2014/15 | a23925 |
| 337-9 | Windward Islands v Canada | Brian Lara Stadium, Tarouba | 2018/19 | a26752 |
| 332-4 | Windward Islands v Bermuda | Melbourne Park, Kingston | 1997/98 | a10720 |
| 300-4 | Windward Islands v Combined Campuses and Colleges | Queen's Park Oval, Port of Spain | 2022/23 | a29478 |
| 296-4 | Windward Islands v Guyana | Queen's Park Oval, Port of Spain | 2022/23 | a29474 |
| 293-8 | Windward Islands v Leeward Islands | Coolidge Cricket Ground, Coolidge | 2016/17 | a25151 |
| 293 | Windward Islands v Hampshire | Three Ws Oval, Cave Hill | 2017/18 | a26166 |
| 286-7 | Windward Islands v Guyana | Coolidge Cricket Ground, Coolidge | 2017/18 | a26185 |
| 284 | Windward Islands v Leeward Islands | Coolidge Cricket Ground, Coolidge | 2020/21 | a28143 |
| 277 | Windward Islands v Combined Campuses and Colleges | Brian Lara Stadium, Tarouba | 2022/23 | a29492 |
| 272-8 | Windward Islands v Guyana | Queen's Park Oval, Port of Spain | 2019/20 | a27796 |
| 268-8 | Windward Islands v Jamaica | Queen's Park Oval, Port of Spain | 2013/14 | a23235 |
| 267-8 | Windward Islands v Combined Campuses and Colleges | Sir Frank Worrell Memorial Ground, St Augustine | 2023/24 | a30316 |
| 266-7 | Windward Islands v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | 2016/17 | a25105 |
| 264 | Windward Islands v United States of America | Brian Lara Stadium, Tarouba | 2019/20 | a27812 |
| 263-6 | Windward Islands v Jamaica | Sabina Park, Kingston | 1988/89 | a5935 |
| 260-8 | Windward Islands v Jamaica | Coolidge Cricket Ground, Coolidge | 2020/21 | a28152 |
| 258-5 | Windward Islands v Guyana | Queen's Park Oval, Port of Spain | 2019/20 | a27768 |
| 256-4 | Windward Islands v Guyana | Tanteen Recreation Ground, St George's | 2006/07 | a17850 |
| 255-7 | Windward Islands v Trinidad and Tobago | Kensington Oval, Bridgetown | 2017/18 | a26149 |
| 254-9 | Windward Islands v Trinidad and Tobago | Queen's Park Oval, Port of Spain | 2023/24 | a30297 |
| 252-5 | Windward Islands v Bermuda | Ronald Webster Park, The Valley | 2000/01 | a12986 |
