| Year | Winner | Work | Nominees |
| 2025 | Ella Langley
Riley Green | “You Look Like You Love Me” |
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| 2024 | Chris Stapleton | "White Horse" | "A Bar Song (Tipsy)" — Shaboozey "Watermelon Moonshine” — Lainey Wilson "Dirt Cheap" — Cody Johnson "I Had Some Help" — Post Malone |
| 2023 | Luke Combs | "Fast Car" | "Heart Like a Truck" — Lainey Wilson "Need a Favor" — Jelly Roll "Next Thing You Know" — Jordan Davis "Wait in the Truck — HARDY |
| 2022 | Cody Johnson | "'Til You Can't" | "Buy Dirt" — Jordan Davis "Half of My Hometown" — Kelsea Ballerini "Never Wanted to Be That Girl" — Carly Pearce and Ashley McBryde "You Should Probably Leave" — Chris Stapleton |
| 2021 | Chris Stapleton | "Starting Over" | "Famous Friends" — Chris Young "The Good Ones" — Gabby Barrett "Hell of a View" — Eric Church "One Night Standards" — Ashley McBryde |
| 2020 | Maren Morris | "The Bones" | "10,000 Hours" — Dan + Shay "Beer Never Broke My Heart" — Luke Combs "Bluebird" — Miranda Lambert "I Hope" — Gabby Barrett |
| 2019 | Blake Shelton | "God's Country" | "Burning Man" — Dierks Bentley "Girl" — Maren Morris "Millionaire" — Chris Stapleton "Speechless" — Dan + Shay |
| 2018 | Chris Stapleton | "Broken Halos" | "Drinkin' Problem" — Midland "Drowns the Whiskey" — Jason Aldean "Meant to Be" — Bebe Rexha "Tequila" — Dan + Shay |
| 2017 | Keith Urban | "Blue Ain't Your Color" | "Better Man" — Little Big Town "Body Like a Back Road" — Sam Hunt "Dirt on My Boots" — Jon Pardi "Tin Man" — Miranda Lambert |
| 2016 | Thomas Rhett | "Die a Happy Man" | "Humble and Kind" — Tim McGraw "My Church" — Maren Morris "Nobody to Blame" — Chris Stapleton "Record Year" — Eric Church |
| 2015 | Little Big Town | "Girl Crush" | "American Kids — Kenny Chesney "I Don't Dance" — Lee Brice "Take Your Time" — Sam Hunt "Talladega" — Eric Church |
| 2014 | Miranda Lambert | "Automatic" | "Drunk on a Plane" — Dierks Bentley "Give Me Back My Hometown" — Eric Church "Meanwhile Back at Mama's" — Tim McGraw "Mine Would Be You" — Blake Shelton |
| 2013 | Florida Georgia Line | "Cruise" | "Highway Don't Care" — Tim McGraw "Mama's Broken Heart" — Miranda Lambert "Merry Go 'Round" — Kacey Musgraves "Wagon Wheel" — Darius Rucker |
| 2012 | Little Big Town | "Pontoon" | "Dirt Road Anthem" — Jason Aldean "God Gave Me You" — Blake Shelton "Home" — Dierks Bentley "Springsteen" — Eric Church |
| 2011 | The Band Perry | "If I Die Young" | "A Little Bit Stronger" — Sara Evans "Colder Weather" — Zac Brown Band "Don't You Wanna Stay" — Jason Aldean "Honey Bee" — Blake Shelton |
| 2010 | Lady Antebellum | "Need You Now" | "A Little More Country Than That" — Easton Corbin "Hillbilly Bone" — Blake Shelton "The House That Built Me" — Miranda Lambert "White Liar" — Miranda Lambert |
| 2009 | Lady Antebellum | "I Run to You" | "Chicken Fried" — Zac Brown Band "In Color" — Jamey Johnson "People Are Crazy" — Billy Currington "Then" — Brad Paisley |
| 2008 | George Strait | "I Saw God Today" | "Don't Blink" — Kenny Chesney "Gunpowder & Lead — Miranda Lambert "Stay" — Sugarland "You're Gonna Miss This" — Trace Adkins |
| 2007 | Carrie Underwood | "Before He Cheats" | "Anyway" — Martina McBride "Lost in This Moment" — Big & Rich "Ticks" — Brad Paisley "Wrapped" — George Strait |
| 2006 | Brooks & Dunn | "Believe" | "Better Life — Keith Urban "Jesus, Take the Wheel" — Carrie Underwood "Summertime" — Kenny Chesney "When I Get Where I'm Going" — Brad Paisley |
| 2005 | Lee Ann Womack | "I May Hate Myself in the Morning" | "Alcohol — Brad Paisley "As Good as I Once Was" — Toby Keith "Baby Girl" — Sugarland "Bless the Broken Road" — Rascal Flatts |
| 2004 | Tim McGraw | "Live Like You Were Dying" | "I Love This Bar" — Toby Keith "Redneck Woman" — Gretchen Wilson "Remember When" — Alan Jackson "Whiskey Lullaby" — Brad Paisley and Alison Krauss |
| 2003 | Johnny Cash | "Hurt" | "Beer for My Horses" — Toby Keith "Celebrity — Brad Paisley "Have You Forgotten?" — Darryl Worley "Three Wooden Crosses" — Randy Travis |
| 2002 | Alan Jackson | "Where Were You (When the World Stopped Turning)" | "Blessed" — Martina McBride "Courtesy of the Red, White and Blue (The Angry American)" — Toby Keith "Drive (For Daddy Gene)" — Alan Jackson "I'm Gonna Miss Her (The Fishin' Song)" — Brad Paisley |
| 2001 | The Soggy Bottom Boys | "Man of Constant Sorrow" | "Ain't Nothing 'bout You" — Brooks & Dunn "Born to Fly" — Sara Evans "I'm Already There" — Lone Star "One More Day" — Diamond Rio |
| 2000 | Lee Ann Womack Sons of the Desert | "I Hope You Dance" |
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| 1999 | Dixie Chicks | "Wide Open Spaces" | "Amazed" — Lonestar "Choices" — George Jones "Don't Laugh at Me" — Mark Wills "Please Remember Me" — Tim McGraw |
| 1998 | Steve Wariner | "Holes in the Floor of Heaven" | "A Broken Wing" — Martina McBride "I Just Want to Dance with You" — George Strait "This Kiss" — Faith Hill "You Don't Seem to Miss Me" — Patty Loveless |
| 1997 | Deana Carter | "Strawberry Wine" | "All the Good Ones Are Gone" — Pam Tillis "Carried Away" — George Strait "It's Your Love" — Tim McGraw "One Night at a Time" — George Strait |
| 1996 | George Strait | "Check Yes or No" | "Blue" — LeAnn Rimes "Go Rest High on That Mountain" — Vince Gill "My Maria" — Brooks & Dunn "Time Marches On" — Tracy Lawrence |
| 1995 | Alison Krauss & Union Station | "When You Say Nothing at All" | "Any Man of Mine" — Shania Twain "Baby Likes to Rock It" — The Tractors "Gone Country" — Alan Jackson "The Keeper of the Stars" — Tracy Byrd |
| 1994 | John Michael Montgomery | "I Swear" | "Does He Love You" — Reba McEntire and Linda Davis "Don't Take the Girl" — Tim McGraw "He Thinks He'll Keep Her" — Mary Chapin Carpenter "How Can I Help You Say Goodbye" — Patty Loveless |
| 1993 | Alan Jackson | "Chattahoochee" | "Ain't That Lonely Yet" — Dwight Yoakam "Don't Let Our Love Start Slippin' Away" — Vince Gill "I Don't Need Your Rockin' Chair" — George Jones "Two Sparrows in a Hurricane" — Tanya Tucker |
| 1992 | Billy Ray Cyrus | "Achy Breaky Heart" | "I Feel Lucky" — Mary Chapin Carpenter "Look at Us" — Vince Gill "Love, Me" — Collin Raye "Maybe It Was Memphis" — Pam Tillis |
| 1991 | Garth Brooks | "Friends in Low Places" | "Don't Rock the Jukebox" — Alan Jackson "Don't Tell Me What to Do" — Pam Tillis "Here's a Quarter (Call Someone Who Cares)" — Travis Tritt "Pocket Full of Gold" — Vince Gill |
| 1990 | Vince Gill | "When I Call Your Name" | "Here in the Real World" — Alan Jackson "If Tomorrow Never Comes" — Garth Brooks "Killin' Time" — Clint Black "Where've You Been" — Kathy Mattea |
| 1989 | Keith Whitley | "I'm No Stranger to the Rain" | "A Better Man" — Clint Black "After All This Time" — Rodney Crowell "Chiseled in Stone" — Vern Gosdin "I'll Leave This World Loving You" — Ricky Van Shelton |
| 1988 | Kathy Mattea | "Eighteen Wheels and a Dozen Roses" | "Do Ya" — K. T. Oslin "I Told You So" — Randy Travis "Somebody Lied" — Ricky Van Shelton "Tennessee Flat Top Box" — Rosanne Cash |
| 1987 | Randy Travis | "Forever and Ever, Amen" | "All My Ex's Live in Texas" — George Strait "Can't Stop My Heart from Loving You" — The O'Kanes "The Right Left Hand" — George Jones "Walk the Way the Wind Blows" — Kathy Mattea |
| 1986 | Dan Seals | "Bop" | "Grandpa (Tell Me 'Bout the Good Ol' Days)" — The Judds "Nobody in His Right Mind Would've Left Her" — George Strait "On the Other Hand" — Randy Travis "Whoever's in New England" — Reba McEntire |
| 1985 | The Judds | "Why Not Me" | "Baby's Got Her Blue Jeans On" — Mel McDaniel "Country Boy" — Ricky Skaggs "Does Fort Worth Ever Cross Your Mind" — George Strait "Highwayman" — The Highwaymen |
| 1984 | Anne Murray | "A Little Good News" | "Holding Her and Loving You" — Earl Thomas Conley "Islands in the Stream" — Kenny Rogers and Dolly Parton "Mama He's Crazy" — The Judds "To All the Girls I've Loved Before" — Julio Iglesias and Willie Nelson |
| 1983 | John Anderson | "Swingin'" | "Heartbroke" — Ricky Skaggs "I Always Get Lucky with You" — George Jones "I.O.U." — Lee Greenwood "Pancho and Lefty" — Merle Haggard and Willie Nelson |
| 1982 | Willie Nelson | "Always on My Mind" | "Crying My Heart Out Over You" — Ricky Skaggs "I'm Gonna Hire a Wino to Decorate Our Home" — David Frizzell "It Turns Me Inside Out" — Lee Greenwood "Love in the First Degree" — Alabama |
| 1981 | Oak Ridge Boys | "Elvira" | "I Believe in You" — Don Williams "I Was Country When Country Wasn't Cool" — Barbara Mandrell "Old Flame" — Alabama "Somebody's Knockin'" — Terri Gibbs |
| 1980 | George Jones | "He Stopped Loving Her Today" | "All the Gold in California" — Larry Gatlin and the Gatlin Brothers "Coward of the County" — Kenny Rogers "Good Ole Boys Like Me" — Don Williams "In America" — Charlie Daniels Band |
| 1979 | Charlie Daniels Band | "The Devil Went Down to Georgia" | "Amanda" — Waylon Jennings "If Loving You Is Wrong (I Don't Want to Be Right)" — Barbara Mandrell "The Gambler" — Kenny Rogers "You Needed Me" — Anne Murray |
| 1978 | The Kendalls | "Heaven's Just a Sin Away" | "Blue Bayou" — Linda Ronstadt "Here You Come Again" — Dolly Parton "Mammas Don't Let Your Babies Grow Up to Be Cowboys" — Waylon Jennings and Willie Nelson "Take This Job and Shove It" — Johnny Paycheck |
| 1977 | Kenny Rogers | "Lucille" | "It Was Almost Like a Song" — Ronnie Milsap "Luckenbach, Texas (Back to the Basics of Love)" — Waylon Jennings "Margaritaville" — Jimmy Buffett "Southern Nights" — Glen Campbell |
| 1976 | Waylon Jennings Willie Nelson | "Good Hearted Woman" |
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| 1975 | Freddy Fender | "Before the Next Teardrop Falls" | "(Hey Won't You Play) Another Somebody Done Somebody Wrong Song" — B. J. Thomas "I'm Not Lisa" — Jessi Colter "Rhinestone Cowboy" — Glen Campbell "Thank God I'm a Country Boy" — John Denver |
| 1974 | Cal Smith | "Country Bumpkin" | "As Soon as I Hang Up the Phone" — Conway Twitty and Loretta Lynn "If You Love Me (Let Me Know)" — Olivia Newton—John "The Most Beautiful Girl" — Charlie Rich "The Streak" — Ray Stevens |
| 1973 | Charlie Rich | "Behind Closed Doors" | "(Old Dogs, Children and) Watermelon Wine" — Tom T. Hall "Satin Sheets" — Jeanne Pruett "The Lord Knows I'm Drinking" — Cal Smith "Why Me" — Kris Kristofferson |
| 1972 | Donna Fargo | "The Happiest Girl in the Whole U.S.A." | "Four in the Morning" — Faron Young "Kiss an Angel Good Mornin'" — Charley Pride "One's on the Way" — Loretta Lynn "To Get to You" — Jerry Wallace |
| 1971 | Sammi Smith | "Help Me Make It Through the Night" | "Amos Moses" — Jerry Reed "Easy Loving" — Freddie Hart "Rose Garden" — Lynn Anderson "When You're Hot, You're Hot" — Jerry Reed |
| 1970 | Merle Haggard | "Okie from Muskogee" | "The Fightin' Side of Me" — Merle Haggard "Hello Darlin'" — Conway Twitty "(I'm So) Afraid of Losing You Again" — Charley Pride "My Woman, My Woman, My Wife" — Marty Robbins |
| 1969 | Johnny Cash | "A Boy Named Sue" | "All I Have to Offer You (Is Me)" — Charley Pride "Daddy Sang Bass" — Johnny Cash "Galveston" — Glen Campbell "Games People Play" — Freddy Weller |
| 1968 | Jeannie C. Riley | "Harper Valley PTA" | "By the Time I Get to Phoenix" — Glen Campbell "D-I-V-O-R-C-E" — Tammy Wynette "Folsom Prison Blues" — Johnny Cash "Honey" — Bobby Goldsboro |
| 1967 | Jack Greene | "There Goes My Everything" | "Danny Boy" — Ray Price "It's Such a Pretty World Today" — Wynn Stewart "Ode to Billie Joe" — Bobbie Gentry "The Fugitive" — Merle Haggard |