List of Awardees
| 2015 | Crystal Gayle | Cliffie Stone Pioneer Award |
| 2015 | Tanya Tucker | Cliffie Stone Pioneer Award |
| 2015 | Statler Brothers | Cliffie Stone Pioneer Award |
| 2014 | none | |
| 2013 | Bob Beckham | Cliffie Stone Pioneer Award |
| 2012 | The Judds (Naomi & Wynonna) | Cliffie Stone Pioneer Award |
| 2012 | Keith Whitley | Cliffie Stone Pioneer Award |
| 2011 | Emmylou Harris | Cliffie Stone Pioneer Award |
| 2011 | Billy Sherrill | Cliffie Stone Pioneer Award |
| 2011 | Ricky Skaggs | Cliffie Stone Pioneer Award |
| 2011 | Dwight Yoakam | Cliffie Stone Pioneer Award |
| 2010 | Garth Brooks | Cliffie Stone Pioneer Award |
| 2010 | Larry Gatlin & the Gatlin Brothers | Cliffie Stone Pioneer Award |
| 2009 | Marty Robbins | Cliffie Stone Pioneer Award |
| 2009 | Mel Tillis | Cliffie Stone Pioneer Award |
| 2008 | Hank Williams, Jr. | Cliffie Stone Pioneer Award |
| 2008 | Jerry Reed | Cliffie Stone Pioneer Award |
| 2008 | Kenny Rogers | Cliffie Stone Pioneer Award |
| 2008 | Randy Travis | Cliffie Stone Pioneer Award |
| 2007 | Brenda Lee | Cliffie Stone Pioneer Award |
| 2007 | Conway Twitty | Cliffie Stone Pioneer Award |
| 2007 | Oak Ridge Boys | Cliffie Stone Pioneer Award |
| 2007 | Porter Wagoner | Cliffie Stone Pioneer Award |
| 2006 | Dolly Parton | Pioneer Award |
| 2006 | Don Williams | Pioneer Award |
| 2006 | Harlan Howard | Pioneer Award |
| 2006 | Waylon Jennings | Pioneer Award |
| 2005 | Bill Monroe | Pioneer Award |
| 2005 | Earl Scruggs | Pioneer Award |
| 2005 | Kris Kristofferson | Pioneer Award |
| 2005 | Little Jimmy Dickens | Pioneer Award |
| 2004 | Chris Le Doux | Pioneer Award |
| 2003 | Ray Price | Pioneer Award |
| 2002 | Alabama | Pioneer Award |
| 2001 | Ronnie Milsap | Pioneer Award |
| 2000 | Barbara Mandrell | Pioneer Award |
| 1999 | Tammy Wynette | Pioneer Award |
| 1998 | Glen Campbell | Pioneer Award |
| 1997 | Charlie Daniels | Pioneer Award |
| 1996 | Roy Clark | Pioneer Award |
| 1995 | Merle Haggard | Pioneer Award |
| 1994 | Loretta Lynn | Pioneer Award |
| 1993 | Charley Pride | Pioneer Award |
| 1992 | George Jones | Pioneer Award |
| 1991 | Willie Nelson | Pioneer Award |
| 1990 | Johnny Cash | Pioneer Award |
| 1989 | ||
| 1988 | Buck Owens | Pioneer Award |
| 1987 | Roger Miller | Pioneer Award |
| 1986 | Minnie Pearl | Pioneer Award |
| 1985 | Kitty Wells | Pioneer Award |
| 1984 | Roy Acuff | Pioneer Award |
| 1983 | Eddy Arnold | Pioneer Award |
| 1982 | Chet Atkins | Pioneer Award |
| 1981 | Leo Fender | Pioneer Award |
| 1980 | Ernest Tubb | Pioneer Award |
| 1979 | Patti Page | Pioneer Award |
| 1978 | Eddie Dean | Pioneer Award |
| 1977 | Sons of the Pioneers | Pioneer Award |
| 1976 | Owen Bradley | Pioneer Award |
| 1975 | Roy Rogers | Pioneer Award |
| 1974 | Johnny Bond | Pioneer Award |
| 1974 | Merle Travis | Pioneer Award |
| 1974 | Tennessee Ernie Ford | Pioneer Award |
| 1973 | Hank Williams Sr. | Pioneer Award |
| 1972 | Cliffie Stone | Pioneer Award |
| 1972 | Gene Autry | Pioneer Award |
| 1971 | Bob Nolan | Pioneer Award |
| 1971 | Stuart Hamblen | Pioneer Award |
| 1971 | Tex Williams | Pioneer Award |
| 1970 | Patsy Montana | Pioneer Award |
| 1970 | Tex Ritter | Pioneer Award |
| 1969 | Bob Wills | Pioneer Award |
| 1968 | Art Satherly | Pioneer Award |