1 Country Song of the Year – "Lost in the Fifties Tonight"Country Music Association*1974 Male Vocalist of the Year*1975 Album of the Year – "A Legend in My Time"*1976 Male Vocalist of the Year*1977 Album of the Year – "Ronnie Milsap Live"*1977 Entertainer of the Year*1977 Male Vocalist of the Year*1978 Album of the Year – "It Was Almost Like a Song"*1986 Album of the Year – "Lost in the Fifties TonightCountry Music Hall of Fame 2014 InducteeGrammy awards*1975 Best Male Country Vocal Performance – "Please Don't Tell Me How The Story Ends"*1977 Best Male Country Vocal Performance – "(I'm a) Stand by My Woman Man"*1982 Best Male Country Vocal Performance – "(There's) No Gettin' Over Me"*1986 Best Male Country Vocal Performance – "Lost in the Fifties Tonight"*1987 Best Male Country Vocal Performance – "Lost in the Fifties Tonight"*1988 Best Country Collaboration with Vocals – "Make No Mistake, She's Mine" (w/ Kenny Rogers)Music City News Country*1975 Most Promising Male ArtistMiscellaneous achievements*40 No.
1 Country Song of the Year - "Lost in the Fifties Tonight"Country Music Association* 1974 Male Vocalist of the Year* 1975 Album of the Year - "A Legend in My Time"* 1976 Male Vocalist of the Year* 1977 Album of the Year - "Ronnie Milsap Live"* 1977 Entertainer of the Year* 1977 Male Vocalist of the Year* 1978 Album of the Year - "It Was Almost Like a Song"* 1986 Album of the Year - "Lost in the Fifties Tonight* 1975 Best Male Country Vocal Performance - "Please Don't Tell Me How The Story Ends"* 1977 Best Male Country Vocal Performance - "(I'm a) Stand By My Woman Man"* 1982 Best Male Country Vocal Performance - "(There's) No Gettin' Over Me"* 1986 Best Male Country Vocal Performance - "Lost in the Fifties Tonight"* 1987 Best Male Country Vocal Performance - "Lost in the Fifties Tonight"* 1988 Best Country Collaboration with Vocals - "Make No Mistake, She's Mine" (w/ Kenny Rogers)Music City News Country* 1975 Most Promising Male ArtistMiscellaneous achievements* 40 No.