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1999 CMA Awards The 33nd Annual Country Music Association Awards were presented September 22, 1999 at Nashville's Grand Ole Opry House. | Entertainer of the Year: | Shania Twain | | Single of the Year: | “Wide Open Spaces,” Dixie Chicks | | Album of the Year: | A Place in the Sun, Tim McGraw | | Song of the Year: | “This Kiss,” Robin Lerner and Beth Nielsen Chapman | | Male Vocalist of the Year: | Tim McGraw | | Female Vocalist of the Year: | Martina McBride | | Vocal Group of the Year: | Dixie Chicks | | Vocal Duo of the Year: | Brooks & Dunn | | Vocal Event of the Year: | “My Kind of Woman/My Kind of Man,” Vince Gill with Patty Loveless | | Horizon Award: | Jo Dee Messina | | Musician of the Year: | Randy Scruggs | | Music Video of the Year: | “Wide Open Spaces,” Dixie Chicks |
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