Special Awards Humanitarian Award Awards 2021 Humanitarian Award 2017 Rock Album of the Year Man Machine Poem 2017 Group of the Year 2013 Music DVD of the Year Bobcaygeon 2006 Music DVD of the Year Hipeponymous - The Tragically Hip 2005 Canadian Music Hall of Fame 2001 Best Rock Album Music @ Work 2000 Best Single Bobcaygeon 1999 Best Rock Album Phantom Power 1997 Album of the Year Trouble at the Henhouse 1997 Group of the Year 1997 North Star Rock Album of the Year Trouble at the Henhouse 1995 Entertainer of the Year 1995 Group of the Year 1993 Canadian Entertainer of the Year 1991 Canadian Entertainer of the Year 1990 Most Promising Group of the Year