| R |
- Yank Rachel: 1987
- Randy Raine-Reusch: 1980, 1981, 1983, 1985
- Steve Rain: 2007
- Ranch Romance: 1990
- The Rankin Family: 1991
- The Rankins: 1999
- Rare Air: 1987
- Rault Brothers Band: 1988
- Lional Rault: 1989, 1992, 1996, 1999
- Rawlins Cross: 1993
- David Rea: 2000
- Eddi Reader: 2001
- Tochi Reagon: 1994
- Red Clay Ramblers: 1984
- Paul Reddick and the Sidemen: 2002
- Red Thunder (Chadi K'azi) Native Dance Theatre: 1996
- Red Thunder Cultural Society: 1992
- Preston Reed: 1989
- Rusty Reed: 1989, 1991
- Reel Union: 1982
- The Reel World String Band: 1985
- Reilly & Maloney: 1983
- John Reischman: 1995
- John Reischman and the Jaybirds (BC/USA): 2004
- John Renbourne: 1987, 1994
- Kimmie Rhodes: 1999, 2000
- Sonny Rhodes: 1988, 2000
- Édouard Richard (QC): 2005
- Zachary Richard: 1991
- Riders in the Sky: 1983, 1985
- Steve Riley and the Mamou Playboys: 2006
- Tracy Riley: 1995
- Josh Ritter (USA): 2005
- River City Ramblers: 1981
- Rizwan-Muazzam Qawwali: 2000
- The Duke Robillard Band: 1996, 1998, 2001
- The Rockin' Highliners: 1999
- Rodrigo Y Gabriela: 2006
- Gamble Rogers: 1983
- Garnet Rogers (ON): 1984, 1989, 2000, 2004
- Roy Rogers and Norton Buffalo (USA): 2005
- Roy Rogers & Shana Morrison: 1999
- Stan Rogers: 1980, 1981, 1982
- The Romaniacs: 1987
- The Romaniuk Family: 1981
- Linda Ronstadt: 2006
- Betsy Rose & Cathy Winter: 1982
- Bev Ross: 1980, 1983, 1986
- Don Ross: 1993, 1998
- Dr. Ross: 1988
- Leon Rosselson: 1985
- Karl Roth: 1992
- Peter Rowan: 1990, 2006
- Peter Rowan & Mark O'Connor: 1984, 1987
- Peter Rowan and the Rowan Brothers: 1994
- Tom Russell: 1987, 1991, 1992, 1999, 2003
- The Tom Russell Band: 1988
- Tom Russell and Andrew Hardin: 1996
- Tom Russell, Barrence Whitfield, Andrew Hardin: 1994
- Justin Rutledge (ON): 2007
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