Country Stars with the Most CMA Award Wins - Page 14

The Country Music Association Awards has been a fixture in country music since its first show, which was untelevised, in 1967. The awards show has almost exclusively taken place in Nashville, aside from 2005’s show at Madison Square Garden in New York City.

Many musicians have etched their names into the history of the genre by the hearing their names called onstage and walking up to accept the trophy, a reward for their contributions in furthering the development of country music. While hundreds have won a CMA award, there’s a group of artists that audiences have heard their names called time and time again.

Here’s 32 country artists with the most CMA award wins in the show’s history, from 1967 through 2025.

This list has been updated to reflect the results of the 59th Annual CMA Awards show.

32. Old Dominion

Wins: 7

Old Dominion has dominated the “Vocal Group of the Year” category, having taken home every single award since 2018 – the longest streak in the CMA’s history. The band was nominated again in 2025.

31. Brothers Osborne

Wins: 7

Brothers Osborne has been a major contender for “Vocal Duo of the Year” for the past decade, with six of their seven CMA awards coming from the category. They’ve won the award three years in a row twice, and are nominated for it again in 2025.

30. Carrie Underwood

Wins: 7

Carrie Underwood took her breakout from American Idol and became one of the most highly-respected country artists during the 21st Century. She’s won “Female Vocalist of the Year” five times, which places her at second in the category all time.

29. Rascal Flatts

Wins: 7

Rascal Flatts has been another dominant group in the “Vocal Group of the Year” category, winning it six years in a row, from 2003 to 2008. The group received their 14th nomination in the category in 2025.

28. George Jones

Wins: 7

George Jones broke out in the 1950s and 1960s before the CMA Awards’ inaugural show. After experiencing a decline into the 1970s, Jones experienced a resurgence in popularity into the 1980s and 1990s, which the CMAs recognized. He won a few CMA awards in the 1990s, and is also tied for sixth in the “Musical Event of the Year” category, with three.

27. Hank Williams Jr.

Wins: 7

Hank Williams Jr. is a two-time “Entertainer of the Year” winner, and dominated the “Video of the Year” category in its early years, when it was introduced in 1985.

26. Alabama

Wins: 7

Alabama was one of the biggest groups in country music during the 1980s, which culminated in three “Entertainer of the Year” award wins. The group is the only non-solo artist to win CMA’s highest honor multiple times.

25. Little Big Town

Wins: 8

Little Big Town dominated the “Vocal Group of the Year” category during the 2010s, winning the award six consecutive times between 2012 and 2017, making them the last group not named “Old Dominion” to win the award. They’ve been nominated for the award every year since 2006.

24. Taylor Swift

Wins: 8

Taylor Swift hasn’t crossed back into country music for quite a while now, but as one of the world’s biggest musicians ever, she’s certainly left her mark on the CMA Awards. The 2009 “Entertainer of the Year” has won in every major category that she’s been eligible for, except the “Single of the Year Award.”

23. Allison Krauss

Wins: 8

Alison Krauss is one of the more unique artists on this list, as she was more of a traditional artist when compared to her contemporary peers during her peak recording years. She’s tied for sixth in “Musical Event of the Year” wins, with three.

22. Johnny Cash

Wins: 8

Johnny Cash had one of the more unique runs in the CMA Awards’ history, as he was winning awards in the show’s early years, which includes his “Entertainer of the Year” award win in 1969. After 1969, he wouldn’t win a CMA Award for 34 years – until he picked up three posthumously in 2003.

21. Ronnie Milsap

Wins: 8

Ronnie Milsap achieved the CMA Awards’ highest honor by winning “Entertainer of the Year” in 1977. He’s second all time in the “Album of the Year” category with four wins, and tied for fifth in the “Male Vocalist of the Year” category with three wins.

20. Loretta Lynn

Wins: 8

Loretta Lynn picked up the “Entertainer of the Year” award at the 1972 CMA Awards. She’s also won “Vocal Duo of the Year” four times with Conway Twitty, and “Female Vocalist of the Year” three times.

19. Luke Combs

Wins: 9

Like Wilson, Luke Combs has become one of the most prolific artists in the CMA’s history in a rather short time. Combs is a two-time “Entertainer of the Year” winner.

18. Willie Nelson

Wins: 9

Willie Nelson is one the biggest legends in country music, so it’s no surprise to find his name among the top-30 artists in the CMA’s history. The 1979 “Entertainer of the Year” winner has been winning CMA awards as recently as 2017.

17. Dolly Parton

Wins: 9

The iconic Dolly Parton is the only artist in CMA Awards history to have won “Entertainer of the Year,” “Female Vocalist of the Year,” “Vocal Duo of the Year and “Vocal Group of the Year.” She won the non-solo awards with Porter Wagoner.

16. The Judds

Wins: 9

The Judds have made a lot of history at the CMA Awards. They were the first and only all-female duo to win the “Vocal Duo of the Year” award, and were the first all-female group to win the “Vocal Group of the Year” award. They’re also the only duo to win in the latter category.

15. The Statler Brothers

Wins: 9

The Statler Brothers currently hold the record for the most “Vocal Group of the Year” award wins with nine, although Old Dominion could move within one award of tying them with a win in 2025.

14. The Chicks

Wins: 10

Prior to their 2003 statement criticizing former President George W. Bush, The Chicks were winning a ton of CMA Awards in a short span of time. The all-female group joined Alabama as the only group to win “Entertainer of the Year” in 2000.

13. Blake Shelton

Wins: 11

The 2012 “Entertainer of the Year,” Blake Shelton has won half of his CMA Awards in the “Male Vocalist of the Year” category, with five. He holds the honor of being tied for second in award wins in the category with Vince Gill and George Strait.

12. Kenny Chesney

Wins: 11

Aside from being one of the most-successful artists in the CMA’s history, Kenny Chesney sits at second for the most wins in the “Entertainer of the Year” category.

11. Tim McGraw

Wins: 11

Tim McGraw took home the “Entertainer of the Year” award in 2001, but has been one of the more dominant artists in the “Musical Event of the Year” category, with four wins, putting him in a five-way tie for first with four wins. He earned a win in the category in 1997 with his wife, Faith Hill, for their song “It’s Your Love.”

10. Lainey Wilson

Wins: 12

Lainey Wilson has shot up the CMA Awards’ all-time wins leaderboard since her 2022 “New Artist of the Year” award win. The 2023 and 2025 “Entertainer of the Year” is tied for third in “Female Vocalist of the Year” award wins with four. She also tied Barbara Mandrell for the most “Entertainer of the Year” award wins by a female artist, with two. With three wins in 2025, she moved to 10th on this list.

9. Keith Urban

Wins: 12

Keith Urban is also tied for first in the “Musical Event of the Year” category, with four wins. Urban’s ultimate achievement, however, is winning the “Entertainer of the Year” award twice.

8. Miranda Lambert

Wins: 14

Miranda Lambert stands alone as the leader in CMA Awards won by a female artist, with 14. She’s taken home the “Female Vocalist of the Year” award a record seven times, but has never won the “Entertainer of the Year” or “New Artist of the Year” awards, despite winning in ever other major award category that she’s eligible for.

7. Brad Paisley

Wins: 14

Brad Paisley, the 2010 “Entertainer of the Year,” holds the distinction of leading all other artists in the “Video of the Year” category, with four wins.

6. Garth Brooks

Wins: 14

Garth Brooks has had one of the most impressive runs at the CMA Awards, when compared to his peers. Between 1991 and 2019, he’s won “Entertainer of the Year” a record seven times, leading all other artists.

5. Alan Jackson

Wins: 16

Alan Jackson sits fifth all time in CMA Award wins, but he’s accomplished a feat no other artist has managed to pull off: He won all top five major awards in a single show (Entertainer, Album, Male Vocalist/Female Vocalist/Group/Duo, Single and Song of the Year), which he accomplished at the 2002 CMA Awards. He’s won “Entertainer of the Year” three times.

4. George Strait

Wins: 17

George Strait is a three-time “Entertainer of the Year” and five-time “Male Vocalist of the Year” winner, reflecting the “King of Country Music’s” legendary run as one of the greatest artists in the genre’s history. He’s also the “king” of the “Album of the Year” category, leading all other artists with five wins.

3. Vince Gill

Wins: 18

Vince Gill is high on leaderboards for several CMA Awards categories. Being one of country music’s most-accomplished songwriters, it’s no surprise he sits atop the “Song of the Year” category with four wins.

2. Chris Stapleton

Wins: 19

Chris Stapleton has established himself as one of country music’s most-accomplished artists in a little over a decade, evident by his 19 CMA award wins, something he accomplished at the 2024 show, along with Brooks & Dunn. He also holds the record for the most “Male Vocalist of the Year” awards with eight – three more than the second-place artists. He’s won the award four consecutive times – twice.

1. Brooks & Dunn

Wins: 19

In 1996, Brooks & Dunn achieved what no other duo has ever done; win the “Entertainer of the Year” award. Kix Brooks and Ronnie Dunn have cemented their status as perhaps the greatest duo in country music history with 16 “Duo of the Year” awards, with their most recent in 2025. With their win at the 59th CMA Awards, they sit firmly at the top when it comes to the most CMA Awards won by an artist.