1999 Christian Country Music Awards

Entertainer of the Year  - The Fox Brothers

Male Vocalist of the Year - Mike Manuel

Female Vocalist of the Year - Gayla Earlene

Vocal Duo of the Year - Double Portion

Vocal Group of the Year - CrossCountry

Christian Country Song of the Year - “Wine Into Water,” T. Graham Brown

Mainstream Country Artist of the Year - T. Graham Brown 

New Artist of the Year - John Steed

Musician of the Year - Phil Driscoll

Pioneer Award - Margo Smith

Living Legend - Johnny Cash

Radio Personality of the Year  - Fred Bacher

Radio Station of the Year - WTUN/Dothan, AL

Video of the Year - “Holes In The Floor Of Heaven,” Steve Wariner