The 7th Annual CWI/WIPA Awards was held at the Sandals Grande Antigua Resort & Spa, on August 19, 2019. The full list of awards reads:
- West Indies U-19 Team of the Year: Guyana
- West Indies Rising Stars U-19 Player of the Year: Joshua Bishop
- Atlantic/WIC Player of the Year: Antonio Ganpath
- First Class Team of the Year: Guyana
- Colonial Medical Insurance Super50
- Cup Player of the Year: Yannick Ottley
- West Indies Championship Player of the Year: Rahkeem Cornwall
- Caribbean T20 Player of the Year: Andre Russell
- West Indies Umpire of the Year: Joel Wilson
- West Indies Emerging Player of the Year: Oshane Thomas
- West Indies Top Groundsman: Charles Joseph
- Colonial Medical Insurance West Indies ODI Player of the Year: Shai Hope
- Colonial Medical Insurance West Indies Women’s ODI Player of the Year: Deandra Dottin
- West Indies Test Match Player of the Year: Jason Holder
- West Indies T20 Player of the Year: Keemo Paul
- West Indies Women’s T20 Player of the Year: Deandra Dottin
- CWI/WIPA Outstanding Foundation Award: The Courtney Walsh Foundation
- CWI Lifetime Achievement Award: Keith ‘Tony’ Marshall
- WIPA Lifetime Achievement Award: Sudesh Dhaniram
- West Indies Women’s Player of the Year sponsored by Sandals: Deandra Dottin
- West Indies Player of the Year sponsored by Sandals: Jason Holder