The awards was held at The Jamica Pegasus Hotel on the 5th June 2014, and featured guest speaker The Most Honourable P.J. Patterson.
- Player of the Year: Darren Bravo
- Test Player of the Year: Shivnarine Chanderpaul
- ODI Player of the Year: Dwayne Bravo
- T20I Player of the Year: Sunil Narine
- Emerging Player of the Year: Miguel Cummins
- Women’s Player of the Year: Stafanie Taylor
- WICB Lifetime Achievement Award: Teddy Griffith
- WIPA Lifetime Achievement Award: Lockhart Sebastien
- Regional Team of the Year: Trinidad and Tobago
- Under-19 Team of the Year: Jamaica
- Regional Four Day Player of the Year: Nikita Miller
- Regional 50-Over Player of the Year: Shane Shillingford
- Caribbean T20 Player of the Year: Darren Bravo
- Under-19 Player of the Year: Tagenarine Chanderpaul
- Atlantic/WIPA in the Community Awardee: Patrina Walcott
- Special Award for Chris Gayle on achieving the milestone of 100 Test Matches played
- Special Award for Shivnarine Chanderpaul on achieving the milestone of 150 Test Matches played