At the 58th annual CMA Awards on Nov. 20, two pairings have the chance to earn their first CMA Award for vocal duo of the year—The War and Treaty and Maddie & Tae. But they are up against three duos who each have previously won multiple times in the category: Brooks & Dunn, Dan + Shay and Brothers Osborne.

The Country Music Association’s vocal duo of the year honor was first presented in 1970, three years after the awards show held its inaugural ceremony in 1967. According to the CMA’s official website, the vocal duo of the year award is “based on the musical performance of the duo as a unit on a country single or album release, as well as their overall contribution to country music.” Current rules define a duo as “an act composed of two people, both of whom normally perform together and neither of whom is known primarily as an individual performing artist.”

Until 1988, the vocal duo of the year category was intended to honor collaborations between solo artists, not established duos. That shifted in 1988 when collaborations were moved to the new vocal event of the year category and the vocal duo of the year category focused on established duos.

Nearly all the solo artists who have won multiple times in the category have done so in tandem with the same partner, such as Conway Twitty with Loretta Lynn (four wins) or Kenny Rogers and Dottie West (two wins). An exception is Willie Nelson, who is a three-time winner in the vocal duo of the year category, but each win was with a different duet partner: Waylon Jennings (1976), Merle Haggard (1983) and Julio Iglesias (1984).

Some of country music’s most iconic duet partners were never winners in the category. George Jones and Tammy Wynette were nominated nine times between 1971 and 1981, but never took home a duo of the year trophy. Johnny Cash and June Carter Cash were nominated in 1970 and 1971 but lost both years to Dolly Parton and Porter Wagoner. 1971 was a particularly competitive year in the category, with nominees including Parton/Wagoner, Cash/Carter Cash, Loretta Lynn/Conway Twitty, George Jones/Tammy Wynette and Charlie Louvin/Melba Montgomery. 

Here is a look at the duos that have won the CMA Award for vocal duo of the year multiple times.