2009
Asleep At The Wheel
This award is no longer presented. Swing groups are included in the Duo/Group of the Year category.
2008
Wylie & The Wild West
2007
The Texas Trailhands
2005
The Texas Trailhands
2004
The Texas Trailhands
2002
Hot Club of Cowtown
2001
Asleep At The Wheel