| Song of the Year |
| Year | Song Title | Performer(s) | Songwriter(s) |
| 2000 | "I Hope You Dance" | Lee Ann Womack/Sons of the Desert | Mark D. Sanders/Tia Sellers |
| 1999 | "Amazed" | Lonestar | Marv Green/Aimee Mayo |
| 1998 | "Holes in the Floor of Heaven" | Steve Wariner | Steve Wariner/Billy Kirsch |
| 1997 | "It's Your Love" | Tim McGraw/Faith Hill | Stephony Smith |
| 1996 | "Blue" | LeAnn Rimes | Bill Mack |
| 1995 | "The Keeper of the Stars" | Tracy Byrd | Dickey Lee/Karen Staley/Danny Mayo |
| 1994 | "I Swear" | John Michael Montgomery | Gary Baker/Frank Myers |
| 1993 | "I Love the Way You Love Me" | John Michael Montgomery | Victoria Shaw/Chuck Cannon |
| 1992 | "I Still Believe in You" | Vince Gill | Vince Gill/John Barlow Jarvis |
| 1991 | "Somewhere in My Broken Heart" | Billy Dean | Billy Dean/Richard Leigh |
| 1990 | "The Dance" | Garth Brooks | Tony Arata |
| 1989 | "Where've You Been" | Kathy Mattea | Jon Vezner/Don Henry |
| 1988 | "Eighteen Wheels and a Dozen Roses" | Kathy Mattea | Charles Nelson/Paul Nelson |
| 1987 | "Forever and Ever, Amen" | Randy Travis | Paul Overstreet/Don Schlitz |
| 1986 | "On the Other Hand" | Randy Travis | Paul Overstreet/Don Schlitz |
| 1985 | "Lost in the Fifties" | Ronnie Milsap | Fredericke Darris/Michael Reid/Troy Seals |
| 1984 | "Why Not Me" | The Judds | Harlan Howard/Brent Maher/Sonny Throckmorton |
| 1983 | "The Wind Beneath My Wings" | Gary Morris | Larry Henley/Jeff Silbar |
| 1982 | "Are the Good Times Really Over" | Merle Haggard | Merle Haggard |
| 1981 | "You're the Reason God Made Oklahoma" | David Frizzell/Shelly West | Boudleaux Bryant/Felice Bryant/Larry Collins/James Pinkard |
| 1980 | "He Stopped Loving Her Today" | George Jones | Bobby Braddock/Curly Putman |
| 1979 | "It's a Cheatin' Situation" | Moe Bandy | Sonny Throckmorton/Curly Putman |
| 1978 | "You Needed Me" | Anne Murray | Randy Goodrum |
| 1977 | "Lucille" | Kenny Rogers | Roger Bowling/Hal Bynum |
| 1976 | "Don't the Girls All Get Prettier at Closing Time" | Mickey Gilley | Baker Knight |
| 1975 | "Rhinestone Cowboy" | Glen Campbell | Larry Weiss |
| 1974 | "Country Bumpkin" | Cal Smith | Don Wayne |
| 1973 | "Behind Closed Doors" | Charlie Rich | Kenny O'Dell |
| 1972 | "The Happiest Girl in the Whole U.S.A." | Donna Fargo | Yvonne Silver |
| 1971 | "Easy Lovin'" | Freddie Hart | Freddie Hart |
| 1970 | "For the Good Times" | Ray Price | Kris Kristofferson |