O'Connor has won two Grammy awards; one for his New Nashville Cats album (1992) and another for Appalachian Journey album (2001) with Yo-Yo Ma and Edgar Meyer.[16] He was named Musician of the Year by the Country Music Association six years in a row (from 1991 to 1996).[17] His collaborative single Restless (with Vince Gill, Ricky Skaggs and Steve Wariner) won the 1991 CMA Vocal Event of the Year award.
All Awards/Honors:
2 Grammy awards; 1992 & 2001.[16]
8 Grammy nominations; 1982–2004.
7 CMA awards; 1991–1996.[17]
7 National & Grand Master fiddling championships; 1975–1984.
2 National Guitar championships; 1975 & 1977.
World mandolin championship; 1982.
Frets Magazine Readers Poll Musician of the year; 1983–1987.
Irish-American Top 100; 2005.
Hundreds of regional, state and local awards; 1972–present.