| Year | Association | Category | Result |
|---|
| 2008 | International Bluegrass Music Association[21] | Entertainer of the Year | Won |
| Vocal Group of the Year | Won |
| Male Vocalist Of The Year ("Jamie Dailey") | Won |
| Album Of The Year ("Dailey & Vincent") | Won |
| Song Of The Year ("By the Mark") | Nominated |
| Gospel Recorded Performance Of The Year ("By The Mark") | Won |
| Emerging Artist of the Year | Won |
| Bass Player Of The Year ("Darrin Vincent") | Nominated |
| 2009 | SPBGMA Awards | Bluegrass Album Of The Year ("Dailey & Vincent") | Nominated |
| Bass Fiddle Performer Of The Year ("Darrin Vincent") | Won |
| Contemporary Male Vocalist Of The Year ("Jamie Dailey") | Won |
| Contemporary Gospel Group Of The Year | Won |
| Vocal Group Of The Year | Won |
| Bluegrass Band Of The Year | Won |
| Song Of the Year ("By The Mark") | Won |
| Entertaining Group Of The Year | Nominated |
| Entertainer Of The Year ("Jamie Dailey") | Nominated |
| 2009 | International Bluegrass Music Association | Entertainer of the Year | Won |
| Vocal Group of the Year | Won |
| Male Vocalist Of The Year (Jamie Dailey) | Nominated |
| Album Of The Year ("Brothers From Different Mothers") | Nominated |
| Gospel Recorded Performance of the Year ("On the Other Side") | Won |
| Bass Player Of The Year ("Darrin Vincent") | Nominated |
| 2010 | SPBGMA Awards | Bass Fiddle Performer Of The Year ("Darrin Vincent") | Won |
| Contemporary Male Vocalist Of The Year ("Jamie Dailey") | Won |
| Contemporary Gospel Group Of The Year | Won |
| Vocal Group Of The Year | Won |
| Bluegrass Band Of The Year | Nominated |
| Entertaining Group Of The Year | Nominated |
| Entertainer Of The Year ("Jamie Dailey") | Nominated |
| 2010 | International Bluegrass Music Association | Entertainer of the Year | Won |
| Vocal Group of the Year | Won |
| Male Vocalist Of The Year (Jamie Dailey) | Nominated |
| Album of the Year (Dailey & Vincent Sing the Statler Brothers) | Won |
| Recorded Performance of the Year ("Give This Message To Your Heart w/Larry Stehenson") | Won |
| Gospel Recorded Performance of the Year ("Don't You Wanna Go To Heaven") | Nominated |
| Bass Player Of The Year ("Darrin Vincent") | Nominated |
| 2011 | SPBGMA Awards | Bluegrass Album Of The Year ("Dailey & Vincent: Sing The Statler Brothers") | Won |
| Bass Fiddle Performer Of The Year ("Darrin Vincent") | Won |
| Contemporary Male Vocalist Of The Year ("Jamie Dailey") | Won |
| Contemporary Gospel Group Of The Year | Won |
| Vocal Group Of The Year | Won |
| Bluegrass Band Of The Year | Won |
| Song Of the Year ("Do You Know You Are My Sunshine") | Nominated |
| Entertaining Group Of The Year | Won |
| Entertainer Of The Year ("Jamie Dailey") | Nominated |
| 2011 | International Bluegrass Music Association | Entertainer of the Year | Nominated |
| Vocal Group of the Year | Nominated |
| Male Vocalist Of The Year ("Jamie Dailey") | Nominated |
| 2011 | Grammy Award | Best Country Performance by a Duo or Group with Vocals ("Elizabeth") | Nominated |
| Dove Awards | Bluegrass Album of the Year (Singing from the Heart) | Won |
| 2012 | SPBGMA Awards | Bass Fiddle Performer Of The Year ("Darrin Vincent") | Won |
| Contemporary Male Vocalist Of The Year ("Jamie Dailey") | Won |
| Contemporary Gospel Group Of The Year | Won |
| Vocal Group Of The Year | Won |
| Bluegrass Band Of The Year | Won |
| Entertaining Group Of The Year | Nominated |
| Entertainer Of The Year ("Jamie Dailey") | Won |
| 2012 | International Bluegrass Music Association | Entertainer of the Year | Nominated |
| Vocal Group of the Year | Nominated |
| Male Vocalist Of The Year ("Jamie Dailey") | Nominated |
| 2013 | SPBGMA Awards | Bass Fiddle Performer Of The Year ("Darrin Vincent") | Nominated |
| Contemporary Male Vocalist Of The Year ("Jamie Dailey") | Nominated |
| Contemporary Gospel Group Of The Year | Won |
| Vocal Group Of The Year | Won |
| Bluegrass Band Of The Year | Won |
| Entertaining Group Of The Year | Nominated |
| Entertainer Of The Year ("Jamie Dailey") | Nominated |
| 2013 | Grammy Award | Best Bluegrass Album ("The Gospel Side Of Dailey & Vincent") | Nominated |