| Year | Winner | Work | Nominees |
| 2019 | Blake Shelton | "God's Country" |
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| 2018 | Chris Stapleton | "Broken Halos" | "Drinkin' Problem" - Midland "Drowns the Whiskey" - Jason Aldean ft. Miranda Lambert "Meant to Be" - Bebe Rexha ft. Florida Georgia Line "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 ft. Faith Hill "Mine Would Be You" - Blake Shelton |
| 2013 | Florida Georgia Line | "Cruise" | "Highway Don't Care" - Tim McGraw ft. Taylor Swift and Keith Urban "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 ft. Kelly Clarkson "Honey Bee" - Blake Shelton |
| 2010 | Lady Antebellum | "Need You Now" | "A Little More Country Than That" - Easton Corbin "Hillbilly Bone" - Blake Shelton ft. Trace Adkins "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 ft. Dolly Parton |
| 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 ft. Alison Krauss |
| 2003 | Johnny Cash | "Hurt" | "Beer for My Horses" - Toby Keith ft. Willie Nelson "Celebrity - Brad Paisley "Have You Forgotten?" - Darryl Worley "Three Wooden Crosses" - Randy Travis |
| 2002 | Alan Jackson | "Where Were You " | "Blessed" - Martina McBride "Courtesy of the Red, White and Blue" - Toby Keith "Drive" - Alan Jackson "I'm Gonna Miss Her" - Brad Paisley |
| 2001 | The Soggy Bottom Boys | "I am a 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" |
- "Breathe" - Faith Hill
- "Buy Me a Rose" - Kenny Rogers
- "He Didn't Have to Be" - Brad Paisley
- "How Do You Like Me Now?!" - Toby Keith
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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 ft. George Jones |
| 1997 | Deana Carter | "Strawberry Wine" | "All the Good Ones Are Gone" - Pam Tillis "Carried Away" - George Strait "It's Your Love" - Tim McGraw ft. Faith Hill "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 | "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 ft. 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 " - 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 " - 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 ft. Dolly Parton "Mama He's Crazy" - The Judds "To All the Girls I've Loved Before" - Willie Nelson ft. Julio Iglesias |
| 1983 | John Anderson | "Swingin'" | "Heartbroken" - Ricky Skaggs "I Always Get Lucky with You" - George Jones "I.O.U." - Lee Greenwood "Pancho and Lefty" - Merle Haggard ft. 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 " - 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 ft. Willie Nelson "Take This Job and Shove It" - Johnny Paycheck |
| 1977 | Kenny Rogers | "Lucille" | "It Was Almost Like a Song" - Ronnie Milsap "Luckenbach, Texas" - 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" | "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 " - Olivia Newton-John "The Most Beautiful Girl" - Charlie Rich "The Streak" - Ray Stevens |
| 1973 | Charlie Rich | "Behind Closed Doors" | " Watermelon Wine" - Tom T. Hall "Satin Sheets" - Jeanne Pruett "The Lord Knows I'm Drinking" - Cal Smith "Why Me Lord" - 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 " 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 " - 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 |
