| 1992 winner | 1991 | Unforgettable: With Love | Natalie Cole | Album | 4 | 8 |
| 1993 winner | 1992 | Perfectly Frank | Tony Bennett | Album | | 3 |
| 1994 winner | 1993 | Steppin’ Out | Tony Bennett | Album | | 2 |
| 1995 winner | 1994 | MTV Unplugged | Tony Bennett | Album + Live | | 9 |
| 1996 winner | 1994 | Duets II | Frank Sinatra | Album + Compilation | | 4 |
| 1997 winner | 1995 | Here’s to the Ladies | Tony Bennett | Album | | 3 |
| 1998 winner | 1997 | On Holiday | Tony Bennett | Album | | 3 |
| 1999 winner | 1998 | Patti Page Live at Carnegie Hall | Patti Page | Album + Live | | 1 |
| 2000 winner | 1999 | Bennett Sings Ellington: Hot & Cool | Tony Bennett | Album | | 2 |
| 2001 winner | 2000 | Both Sides Now | Joni Mitchell | Album | 4.35 | 8 |
| 2002 winner | 2001 | Songs I Heard | Harry Connick, Jr. | Album | 3 | 2 |
| 2003 winner | 2001 | Playin’ With My Friends: Bennett Sings the Blues | Tony Bennett | Album | | 3 |
| 2004 winner | 2002 | A Wonderful World | Tony Bennett & k.d. lang | Album | 4 | 7 |
| 2005 winner | 2004 | Stardust… The Great American Songbook, Volume Ⅲ | Rod Stewart | Album | 4 | 5 |
| 2006 winner | 2004 | The Art of Romance | Tony Bennett | Album | | 2 |
| 2007 winner | 2006 | Duets: An American Classic | Tony Bennett | Album | | 8 |
| 2008 winner | 2007 | Call Me Irresponsible | Michael Bublé | Album | 5 | 11 |
| 2009 winner | 2008 | Still Unforgettable | Natalie Cole | Album | | 7 |
| 2010 winner | 2009 | Michael Bublé Meets Madison Square Garden | Michael Bublé | Album + Live | | 5 |
| 2011 winner | 2009 | Crazy Love | Michael Bublé | Album | 4 | 22 |
| 2012 winner | 2011 | Duets II | Tony Bennett | Album | | 7 |
| 2013 winner | 2012 | Kisses on the Bottom | Paul McCartney | Album | 4 | 17 |
| 2014 winner | 2013 | To Be Loved | Michael Bublé | Album | 4.35 | 21 |
| 2015 winner | 2014 | Cheek to Cheek | Tony Bennett & Lady Gaga | Album | 3.25 | 14 |
| 2016 winner | 2015 | The Silver Lining: The Songs of Jerome Kern | Tony Bennett & Bill Charlap | Album | | 2 |
| 2017 winner | 2016 | Summertime: Willie Nelson Sings Gershwin | Willie Nelson | Album | 4 | 2 |
| 2018 winner | 2016 | Tony Bennett Celebrates 90 | Tony Bennett | Album + Live | | 4 |
| 2019 winner | 2018 | My Way | Willie Nelson | Album | 2 | 8 |
| 2020 winner | 2018 | Look Now | Elvis Costello & The Imposters | Album | 5 | 8 |
| 2021 winner | 2020 | American Standard | James Taylor | Album | | 9 |
| 2022 | 2020 | A Holly Dolly Christmas | Dolly Parton | Album | | 9 |
| 2022 | 2020 | A Tori Kelly Christmas | Tori Kelly | Album | 5 | 8 |
| 2022 | 2021 | That’s Life | Willie Nelson | Album | 3.35 | 2 |
| 2022 | 2021 | …’Til We Meet Again | Norah Jones | Album + Live | | 8 |
| 2022 | 2021 | Ledisi Sings Nina | Ledisi | Album | | 1 |
| 2022 winner | 2021 | Love for Sale | Tony Bennett & Lady Gaga | Album | 1.5 | 17 |
| 2023 | 2021 | I Dream of Christmas | Norah Jones | Album | 4.5 | 18 |
| 2023 | 2021 | When Christmas Comes Around… | Kelly Clarkson | Album | | 9 |
| 2023 | 2021 | Evergreen | Pentatonix | Album | 4 | 4 |
| 2023 | 2021 | Thank You | Diana Ross | Album | | 5 |
| 2023 | 2022 | Higher | Michael Bublé | Album | 3.5 | 8 |
| 2024 | 2022 | Holidays Around the World | Pentatonix | Album | | 2 |
| 2024 | 2022 | Only the Strong Survive: Covers, Vol. 1 | Bruce Springsteen | Album | 4 | 23 |
| 2024 | 2022 | To Steve with Love: Liz Callaway Celebrates Sondheim | Liz Callaway | Album + Live | | 1 |
| 2024 | 2022 | Sondheim Unplugged {The NYC Sessions}, Volume Three | Stephen Sondheim | Album + Compilation | | 2 |
| 2024 | 2023 | Pieces of Treasure | Rickie Lee Jones | Album | 3 | 2 |
| 2024 winner | 2023 | Bewitched | Laufey | Album | 3 | 15 |
| 2025 | 2023 | Christmas Wish | Gregory Porter | Album | | 6 |
| 2025 | 2024 | Good Together | Lake Street Dive | Album | | 2 |
| 2025 | 2024 | à Fleur de Peau | Cyrille Aimée | Album | | 3 |
| 2025 | 2024 | IMPOSSIBLE DREAM | Aaron Lazar | Album | | 1 |
| 2025 winner | 2024 | Visions | Norah Jones | Album | 3 | 9 |
| 2026 | 2024 | Harlequin | Lady Gaga | Album + Soundtrack | 2.35 | 10 |
| 2026 | 2024 | The Gift of Love | Jennifer Hudson | Album | | 4 |
| 2026 | 2024 | Wintersongs | Laila Biali | Album | | 1 |
| 2026 | 2025 | Who Believes in Angels? | Elton John & Brandi Carlile | Album | 2 | 6 |
| 2026 | 2025 | The Secret of Life: Partners, Volume 2 | Barbra Streisand | Album | | 6 |
| 2026 winner | 2025 | A Matter of Time | Laufey | Album | 3 | 17 |
