Year | Winner(s) | Album | Nominees | Ref. |
2003 | Diana Krall | Live in Paris | - Coral Egan, the path of least resistance
- Molly Johnson, Another Day
- Susie Arioli Swing Band, Pennies from Heaven
- Joani Taylor and Bob Murphy, The Wall Street Sessions
| |
2004 | Holly Cole | Shade | - Jeri Brown, Firm Roots
- Ranee Lee, Maple Groove
- Denzal Sinclaire, Denzal Sinclaire
- Carol Welsman, The Language of Love
| |
2005 | Diana Krall | The Girl in the Other Room | | |
2006 | Diana Krall | Christmas Songs | | |
2007 | Diana Krall | From This Moment On | - Lori Cullen, Calling for Rain
- Kellylee Evans, Fight or Flight?
- Molly Johnson, Messin' Around
- Elizabeth Shepherd, Start to Move
| |
2008 | Sophie Milman | Make Someone Happy | | |
2009 | Molly Johnson | Lucky | | |
2010 | Ranee Lee | Ranee Lee Lives Upstairs | | |
2011 | Kellylee Evans | Nina | | |
2012 | Sonia Johnson | Le Carré de nos amours | | |
2013 | Emilie-Claire Barlow | Seule ce soir | - Diana Krall, Glad Rag Doll
- Diana Panton, Christmas Kiss
- Elizabeth Shepherd, Rewind
- Carol Welsman, Journey
| |
2014 | Mike Rud ft. Sienna Dahlen | Notes on Montréal | - Matt Dusk, My Funny Valentine: The Chet Baker Songbook
- Sonia Johnson, Charles Biddle Jr. and Annie Poulain, Triades
- Amy McConnell and William Sperandei, Stealing Genius
- Erin Propp with Larry Roy, Courage, My Love
| |
2015 | Diana Panton | Red | - Julie Crochetière, Counting Dreams
- Angela Galuppo, Angela Galuppo
- Molly Johnson, Because of Billie
- Elizabeth Shepherd, The Signal
| |
2016 | Emilie-Claire Barlow | Clear Day | - Dan Brubeck Quartet, Live from the Cellar
- Jaclyn Guillou, This Bitter Earth
- Tara Kannangara, Some Version of the Truth
- Alex Pangman, New
| |
2017 | Bria Skonberg | Bria | - Heather Bambrick, You'll Never Know
- Matt Dusk and Florence K, Quiet Nights
- Barbra Lica, I'm Still Learning
- Amanda Tosoff, Words
| |
2018 | Diana Krall | Turn Up the Quiet | | |
2019 | Laila Biali | Laila Biali | | [2] |
2020 | Dominique Fils-Aimé | Stay Tuned! | - Jazz Affair, Wishes
- Monkey House, Friday
- Elizabeth Shepherd, Montreal
- Bria Skonberg, Nothing Never Happens
| [3] |