Who's won the most trophies in the history of the CMA Awards? ANSWER: While Brooks & Dunn and Vince Gill are both tied with 18 wins each, Ronnie Dunn ultimately comes out on top, because he has one more win for co-writing the 2006 Song of the Year, "Believe." He also took home an extra Single of the Year trophy that same year for producing the song.
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