Awards and Nominations
| Year | Association | Category | Result |
|---|---|---|---|
| 2002 | Canadian Radio Music Awards | Best New Solo Artist (Adult Contemporary) | Won |
| Best New Solo Artist (Country) | Won | ||
| Canadian Country Music Awards | Album of the Year - Song Dog | Won | |
| Roots Artist/Group of the Year | Won | ||
| East Coast Music Awards | Album of the Year - Song Dog | Won | |
| Country Artist/Group of the Year | Won | ||
| Male Artist of the Year | Won | ||
| Single of the Year - "Followed Her Around" | Won | ||
| SOCAN Songwriter of the Year - "Followed Her Around" | Won | ||
| Video of the Year - "Followed Her Around | Won | ||
| Juno Awards of 2002 | Best Country Artist/Group | Nominated | |
| Nova Scotia Music Awards | Music Industry Artist of the Year | Won | |
| Songwriter of the Year | Won | ||
| SOCAN Awards | Single of the Year - "Followed Her Around" | Won | |
| 2003 | East Coast Music Awards | Single of the Year - "Midnight Angel" | Won |
| SOCAN Songwriter of the Year - "Midnight Angel" | Won | ||
| 2004 | East Coast Music Awards | Album of the Year - Handmade | Won |
| Entertainer of the Year | Won | ||
| Male Artist of the Year | Won | ||
| Roots/Traditional Solo Recording of the Year - Handmade | Won | ||
| Single of the Year - "Morning Bound Train" | Won | ||
| SOCAN Songwriter of the Year - "Morning Bound Train" | Won | ||
| 2005 | East Coast Music Awards | Entertainer of the Year | Won |
| Single of the Year - "Butterfly" | Won | ||
| SOCAN Songwriter of the Year - "Butterfly" | Won | ||
| Video of the Year - "Butterfly" | Won | ||
| 2008 | Canadian Country Music Awards | Songwriter of the Year - "First Time in a Long Time" | Won |
| East Coast Music Awards | Country Recording of the Year - Edge of Day | Won | |
| FACTOR Recording of the Year - Edge of Day | Won | ||
| Konica Minolta Male Solo Recording of the Year - Edge of Day | Won | ||
| SOCAN Songwriter of the Year - "Slipping Away" | Won | ||
| 2011 | Canadian Country Music Awards | Roots Artist/Group of the Year | Won |
| Nova Scotia Music Awards | SOCAN Songwriter of the Year - "Here in My Heart" | Won | |
| 2012 | Juno Awards of 2012 | Country Album of the Year - Forget About the World | Nominated |
| East Coast Music Awards | Fan's Choice Video of the Year | Won | |
| Canadian Country Music Awards | Roots Artist/Group of the Year | Won |
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