The Scotland internatioal defender took the award ahead of goalkeeper Ali Al-Habsi in second place and Victor Moses in third.
Speaking to the club's official website regarding the honour, Caldwell said: "It's a fantastic honour to pick up the award and I'd like to thank each and every fan who voted, but they're the real winners this season."Everything the team and I do on the pitch is inspired by them and they deserve the celebrations we hope to see on Sunday afternoon."
Below is a round up of the awards:
Player of the Season - Gary Caldwell
The Players, Player of the Season - Maynor Figueroa
The Away Player of the Season - Ali Al-Habsi
Goal of the Season - Shaun Maloney v Manchester United
Performance of the Season - Win against Manchester United
Outstanding Contribution Award - Emmerson Boyce
Community Achievement Award - Neil Rimmer and Matt Jackson
Young Player of the Season - Tim Chow
Youth Team Player - Ryan Meadows
Fan Of The Season - Brian Sabin