Who Has Won the Most CMA Awards This Century?

In addition to these five awards, the trio won five awards in the ’90s. Their top awards in this century include album of the year for Fly and entertainer of the year (both 2000).

The producer has won all of these awards since 2015, all for his work with Stapleton. His tally includes three awards for album of the year.

The producer has won all of these awards since 2001. The wins include back-to-back awards for single of the year for Thomas Rhett’s “Die a Happy Man” (2016) and Keith Urban’s “Blue Ain’t Your Color” (2017). Huff is nominated for one award this year – musical event of the year for producing “Thank God” by Kane Brown with Katelyn Brown.

Morris, who recently announced that she was moving on from country, has won all of these awards since 2016, when she was named new artist of the year. Her wins include album of the year for Girl (2019).

Musgraves has won all of these awards since 2013, when she was named new artist of the year. Her wins include album of the year for Golden Hour (2018).

The group has won all these awards since 2018. It has won vocal group of the year the last five years running and is nominated in that category again this year. It is also nominated for music video of the year for “Memory Lane.”

The duo has won all of these awards since 2007. All five were for vocal duo of the year. In addition, Jennifer Nettles won an award for song of the year for “Stay.”

The brother duo has won all of these awards since 2016. Their tally includes five wins for vocal duo of the year. They’re nominated in that category again this year.

The trio has won all of these awards since 2008, when they became the first winners of new artist of the year following its name change from the horizon award. Their wins include back-to-back single of the year awards for “I Run to You” (2009) and “Need You Now” (2010). This year, they are nominated for vocal group of the year, an award they have won three times.

These six wins are in addition to 11 that King George won in the ’80s and ’90s. His wins in this century include back-to-back album of the year awards for It Just Comes Natural (2007) and Troubadour (2008).

Womack has won all of these awards since 2000. Her tally includes two awards for single of the year for the tender “I Hope You Dance” (2000) and “I May Hate Myself in the Morning” (2005).

In addition to these seven awards, McGraw won four awards in the ‘90s. His top award in this century is entertainer of the year (2001).

The trio won all of these prizes since 2002, when they won the horizon award. Their other six awards were for vocal group of the year.

Underwood has won all of these awards since 2006, when she won the horizon award. Her tally includes five trophies for female vocalist of the year. This year, she is nominated for entertainer of the year – an award she has yet to win.

In addition to these eight awards, the duo won 10 awards in the 1990s. Kix Brooks & Ronnie Dunn’s wins in this century include single and music video of the year for “Believe” (2006). (In addition, Dunn won one award apart from Brooks for song of the year for co-writing “Believe.”) This year, the duo is nominated for vocal duo of the year – an award it has won 14 total times (six in this century).

Combs has won all of these awards since 2018, when he won new artist of the year. He won album of the year for What You See Is What You Get and Growin’ Up and has won entertainer of the year the last two years running. Combs has four nominations this year – entertainer of the year, single of the year (“Fast Car”), album of the year (Gettin’ Old) and male vocalist of the year.

The quartet has won all of these awards since 2012. Its tally includes two wins for single of the year, for “Pontoon” (2012) and “Girl Crush” (2015). This year it is nominated for vocal group of the year – an award it has won six times.

Jackson has won more CMA Awards in this century than anyone else who landed their first CMA Award in the last century. He won seven CMA Awards in the 1990s. His tally for this century includes back-to-back wins for entertainer of the year (2002-03).

Swift has won all of these awards since 2007, when she won the horizon award. She won twice for entertainer of the year, in 2009 and 2011. (Imagine how high up the list she would be if she hadn’t made a mid-career transition to pop.)

The session guitarist has won all these awards since 2008. They have all come in the musician of the year category.

Shelton has won all of these awards since 2010. His tally includes entertainer of the year (2012) and album of the year for Based on a True Story (2013).

Chesney has landed all these wins since 2004. His tally includes four wins for entertainer of the year.

Urban has landed all of these wins since 2001, when he won the horizon award. His awards include widely separated wins for entertainer of the year (2005 and 2018).

Lambert has amassed all of these wins since 2010. The tally includes two awards for album of the year, for Revolution (2010) and Platinum (2014), and a record seven awards for female vocalist of the year. She is nominated in the latter category again this year.

Paisley has amassed all of these wins since 2000, when he won the horizon award (now called new artist of the year). His wins include album of the year for Time Well Wasted (2006) and entertainer of the year (2010).

Stapleton has amassed all of these wins since 2015, when he won new artist of the year. His tally includes three wins for album of the year for Traveller (2015), From A Room: Volume 1 (2017) and Starting Over (2021). He has three nominations this year – entertainer of the year, musical event of the year (for his featured role on Carly Pearce’s “We Don’t Fight Anymore”) and male vocalist of the year.