She has won two major awards: a Grammy Award for Best Country Collaboration with Vocals in 1999 for the multi-artist collaboration "Same Old Train", and the 1994 Country Music Association award for Female Vocalist of the Year followed by the CMA President's Award in 1998. Tillis has also received two Recorded Event of the Year awards from the International Bluegrass Music Association. Tillis has also earned one of country music's crowning achievements, becoming a member of the Grand Ole Opry, when she was inducted in 2000, 9 years after making her first appearance as a guest artist in 1991. She later inducted her father into the Opry in 2007.