2. Brooks & Dunn –(18) wins total; Vocal Duo of the Year (1992); Vocal Duo of the Year (1993); Album of the Year (1994); Vocal Duo of the Year (1994); Vocal Duo of the Year (1995); Entertainer of the Year (1996); Vocal Duo of the Year (1996); Vocal Duo of the Year (1997); Vocal Duo of the Year (1998); Vocal Duo of the Year (1999); Vocal Duo of the Year (2001); Vocal Duo of the Year (2002); Vocal Duo of the Year (2003); Vocal Duo of the Year (2004); Vocal Duo of the Year (2005); Vocal Duo of the Year (2006); Music Video of the Year (2006); Single of the Year (2006).

3. Vince Gill–(18) wins total; Single of the Year (1990); Male Vocalist of the Year (1991); Song of the Year (1991); Vocal Event of the Year (1991); Male Vocalist of the Year (1992); Song of the Year (1992); Album of the Year (1993); Entertainer of the Year (1993); Male Vocalist of the Year (1993); Song of the Year (1993); Vocal Event of the Year (1993); Album of the Year (1994); Entertainer of the Year (1994); Male Vocalist of the Year (1994); Male Vocalist of the Year (1995); Song of the Year (1996); Vocal Event of the Year (1996); Vocal Event of the Year (1999).

4. George Strait–(17) wins total; Album of the Year (1985); Male Vocalist of the Year (1985); Male Vocalist of the Year (1986); Entertainer of the Year (1989);Entertainer of the Year 1990); Album of the Year (1996); Male Vocalist of the Year (1996); Single of the Year (1996); Album of the Year (1997); Male Vocalist of the Year (1997); Male Vocalist of the Year (1998); Vocal Event of the Year (2000); Musical Event of the Year (2005); Album of the Year (2007); Album of the Year (2008); Single of the Year (2008); Entertainer of the Year (2013).

5. Alan Jackson–(16) wins total; Music Video of the Year (1992); Music Video of the Year (1993); Single of the Year (1993); Vocal Event of the Year (1993); Album of the Year (1994); Song of the Year (1994); Entertainer of the Year (1995); Vocal Event of the Year (2000); Album of the Year (2002); Entertainer of the Year (2002); Male Vocalist of the Year (2002); Single of the Year (2002); Song of the Year (2002); Entertainer of the Year (2003); Male Vocalist of the Year (2003); Vocal Event of the Year (2003).

6. Brad Paisley–(14) wins total; Horizon Award (2000); Vocal Event of the Year (2001); Music Video of the Year (2002); Music Video of the Year (2004); Musical Event of the Year (2004); Album of the Year (2006); Musical Event of the Year (2006); Male Vocalist of the Year (2007); Music Video of the Year (2007); Male Vocalist of the Year (2008); Music Video of the Year (2008); Male Vocalist of the Year (2009); Musical Event of the Year (2009);Entertainer of the Year (2010).

7. Garth Brooks–(13) wins total; Horizon Award (1990); Music Video of the Year (1990); Album of the Year (1991); Entertainer of the Year (1991); Music Video of the Year (1991); Single of the Year (1991); Album of the Year (1992); Entertainer of the Year (1992); Vocal Event of the Year (1993); Entertainer of the Year (1997); Entertainer of the Year (1998); Entertainer of the Year (2016); Entertainer of the Year (2017).

8. Miranda Lambert–(13) wins total; Album of the Year (2010); Female Vocalist of the Year (2010); Music Video of the Year (2010); Female Vocalist of the Year (2011); Female Vocalist of the Year (2012); Song of the Year (2012); Female Vocalist of the Year (2013); Album of the Year (2014); Female Vocalist of the Year (2014); Musical Event of the Year (2014); Single of the Year (2014); Female Vocalist of the Year (2015); Female Vocalist of the Year (2017).

9. Keith Urban–(12) wins total; Horizon Award (2001); Male Vocalist of the Year (2004); Entertainer of the Year (2005); Male Vocalist of the Year (2005); Male Vocalist of the Year (2006); Musical Event of the Year (2009); Music Video of the Year (2013); Musical Event of the Year (2013); Musical Event of the Year (2014); Musical Event of the Year (2015); Single of the Year (2017); Entertainer of the Year (2018).

10. Tim McGraw–(11) wins total; Vocal Event of the Year (1997); Album of the Year (1998); Album of the Year (1999); Male Vocalist of the Year (1999); Male Vocalist of the Year (2000); Entertainer of the Year (2001); Single of the Year (2004); Musical Event of the Year (2007); Musical Event of the Year (2012); Music Video of the Year (2013); Musical Event of the Year (2013).

11. Dixie Chicks–(10) wins total; Horizon Award (1998); Vocal Group of the Year (1998); Music Video of the Year (1999); Single of the Year (1999); Vocal Group of the Year (1999); Album of the Year (2000); Entertainer of the Year (2000); Music Video of the Year (2000); Vocal Group of the Year (2000); Vocal Group of the Year (2002).

12. Mac McAnally–(10) wins total; Musician of the Year (2008); Musician of the Year (2009); Musician of the Year (2010); Musician of the Year (2011); Musician of the Year (2012);Musician of the Year (2013); Musician of the Year (2014); Musician of the Year (2015); Musician of the Year (2017); Musician of the Year (2018).

13. Willie Nelson–(10) wins total; Album of the Year (1976); Single of the Year (1976); Vocal Duo of the Year (1976); Entertainer of the Year (1979); Album of the Year (1982); Single of the Year (1982); Vocal Duo of the Year (1983); Vocal Duo of the Year (1984); Vocal Event of the Year (2002); Musical Event of the Year (2017).

14. Chris Stapleton–(10) wins total; Album of the Year (2015); Male Vocalist of the Year (2015); New Artist of the Year (2015); Male Vocalist of the Year (2016); Music Video of the Year (2016); Album of the Year (2017); Male Vocalist of the Year (2017); Male Vocalist of the Year (2018); Single of the Year (2018); Song of the Year (2018).