| O |
- Tim O'Brien: 1997, 2002
- Tim O'Brien, Darrell Scott, Dirk Powell: 2001
- Tim and Mollie O'Brien and the O'Boys: 1996
- Sinéad O'Connor: 1997
- Odetta: 1980, 1981, 2000
- Liam O'Flynn: 1993
- Mary Margaret O'Hara (ON): 2007
- Oh Susanna (ON): 1997, 2000, 2004
- Danny O'Keefe: 1987
- Old Reliable (AB): 2002, 2005
- Ollabelle (USA): 2007
- One Yellow Rabbit: 1984
- Ndidi Onukwulu (ON): 2007
- Open Mind: 1992
- The Original Balkan Jam: 1984, 1985, 1986
- Joan Osborne: 1998, 2001
- Oysterband (UK): 1987, 1991, 1997, 2001, 2005
- Ozomatli (USA): 2007
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