The 1999 awards show was on Wednesday September 22nd, and was the 33rd annual awards. They were hosted by Vince Gill. The televised show attracted an audience of 37 million viewers.

   For each category the winner is listed first, followed by the other nominees

Entertainer of the Year

    Shania Twain
    Garth Brooks
    George Strait
    Tim McGraw
    Dixie Chicks

Male Vocalist of the Year

    Tim McGraw
    Vince Gill
    Alan Jackson
    George Strait
    Steve Wariner

Female Vocalist of the Year

    Martina McBride
    Faith Hill
    Jo Dee Messina
    Shania Twain
    Trisha Yearwood

Horizon Award

    Jo Dee Messina
    Kenny Chesney
    Sara Evans
    Wilkinsons
    Chely Wright

Vocal Group of the Year

    Dixie Chicks
    Alabama
    Diamond Rio
    Lonestar
    Wilkinsons

Vocal Duo of the Year

    Brooks & Dunn
    The Kinleys
    The Lynns
    Montgomery Gentry
    The Warren Brothers

Album of the Year

    A Place In The Sun
      Tim McGraw
      Curb Records
      Produced by Tim McGraw/Byron Gallimore/James Stroud
    Always Never The Same
      George Strait
      MCA Records
      Produced by George Strait/Tony Brown
    The Key
      Vince Gill
      MCA Records
      Produced by Tony Brown
    Two Teardrops
      Steve Wariner
      Capitol Nashville
      Produced by Steve Wariner
    Where Your Road Leads
      Trisha Yearwood
      MCA Records
      Produced by Trisha Yearwood/Tony Brown

Musician of the Year

    Randy Scruggs - Guitar
    Brent Mason - Guitar
    Eddie Bayers - Drums
    Paul Franklin - Steel Guitar
    Dan Huff - Guitar

Single of the Year

    "Wide Open Spaces" Dixie Chicks - Monument Produced by Paul Worley/Blake Chancey
    "Amazed" Lonestar - BNA Records Produced by Dann Huff
    "Choices" George Jones - Asylum Produced by Keith Stegall
    "Don't Laugh At Me" Mark Wills - Mercury Produced by Carson Chamberlain
    "Please Remember Me" Tim McGraw - Curb Records Produced by James Stroud/Byron Gallimore/Tim McGraw

Vocal Event of the Year

    Vince Gill with Patty Loveless "My Kind of Woman/My Kind of Man" MCA Records
    Waylon Jennings, Mel Tillis, Bobby Bare, Jerry Reed Old Dogs Atlantic Records
    Sara Evans with Vince Gill "No Place That Far" RCA Records
    Emmylou Harris, Linda Ronstadt and Dolly Parton Trio II Asylum Records
    Clint Black, Joe Diffie, Merle Haggard, Emmylou Harris, Alison Krauss, Patty Loveless, Earl Scruggs, Ricky Skaggs, Marty Stuart, Pam Tillis, Randy Travis, Travis Tritt and Dwight Yoakam "Same Old Train" Col

Song of the Year

    "This Kiss" Beth Nielsen Chapman/Annie Roboff/Robin Lerner Puckalesia Songs/Nomad-Noman Music/Warner-Tamerlane Pub./Almo Music/Anwa Music/BNC Songs
    "Don't Laugh At Me" Allen Shamblin/Steve Seskin Built on Rock Music/David Aaron Music/Love This Town Music
    "Husbands and Wives" Roger Miller Sony/ATV Songs
    "If You Ever Have Forever In Mind" Vince Gill/Troy Seals Vinny Mae Music/Irvin Music/Baby Dumplin Music
    "Please Remember Me" Rodney Crowell/Will Jennings Blue Sky Rider Songs/Sony ATV Tunes

Music Video of the Year

    Wide Open Spaces
      Directed by Thom Oliphant
      Performed by the Dixie Chicks
    Don't Laugh At Me
      Directed by Jim Hershleder
      Performed by Mark Wills
    How Forever Feels
      Directed by Martin Kahan
      Performed by Kenny Chesney
    I'll Go On Loving You
      Directed by Steven Goldmann
      Performed by Alan Jackson
    Just To Hear You Say That You Love Me
      Directed by Jim Shea
      Performed by Faith Hill with Tim McGraw