All Grammy Awards and
Nominations for Bobby Osborne
| Year | Award | Artists | Work | All Nominees |
|---|---|---|---|---|
| 2018 | Best Bluegrass Album | Bobby Osborne | Original | All Nominees |
| 2007 | Best Country Collaboration with Vocals | Rhonda Vincent, Bobby Osborne | Midnight Angel | All Nominees |
| 2000 | Best Bluegrass Album | Sam Bush, David Grisman, Ronnie McCoury, Jesse McReynolds, Bobby Osborne, Ricky Skaggs, Frank Wakefield, Buck White, Del McCoury | Bluegrass Mandolin Extravaganza (Album) | All Nominees |
| 1995 | Best Bluegrass Album | Osborne Brothers | When The Roses Bloom In Dixieland (Album) | All Nominees |
| 1992 | Best Bluegrass Album | Osborne Brothers | Hillbilly Fever (Album) | All Nominees |
| 1992 | Best Country Instrumental Performance | Osborne Brothers | Orange Blossom Special (Track) | All Nominees |
| 1980 | Best Country Instrumental Performance | Osborne Brothers | Bluegrass Concerto (Album) | All Nominees |
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