| 100% | MARYJ | 5 | Grammy winner ___ Blige: 2 wds. |
| 73% | ANDERSONPAAK | 12 | "Bubblin" Grammy winner: 2 wds. |
| 64% | MUNILONG | 8 | 2023 Best R&B Performance Grammy winner for "Hrs & Hrs": 2 wds. |
| 63% | BRUNOMARS | 9 | "That's What I Like" Grammy winner: 2 wds. |
| 62% | MARYJ | 5 | Grammy winner Blige |
| 62% | PATBENATAR | 10 | 1981 Grammy winner for "Fire and Ice" (Best Rock Vocal Performance, Female): 2 wds. |
| 56% | CARLOSSANTANA | 13 | Ten-time Grammy winner who was born July 20, 1947 (2 wds.) |
| 54% | HARRYSTYLES | 11 | "Watermelon Sugar" Grammy winner who plays constable Tom Burgess in "My Policeman" (2 wds.) |
| 54% | DANANDSHAY | 10 | "Tequila" Grammy winners who are coaches on season 25 of "The Voice" (2 wds.) |
| 53% | LEVARBURTON | 11 | "Reading Rainbow" host who was the first Grammy winner to guest-host "Jeopardy!" (2 wds.) |
| 53% | MIRANDALAMBERT | 14 | "Wildcard" Best Country Album Grammy winner who was born on November 10, 1983 (2 wds.) |
| 52% | BONNIERAITT | 11 | 10-time Grammy winner whose self-titled debut album includes the song "Thank You" (2 wds.) |
| 52% | JOHNLEGEND | 10 | "Ordinary People" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 51% | GETLUCKY | 8 | 2013 Record of the Year Grammy winner by Daft Punk featuring 15-Across/52-Across (2 wds.) |
| 50% | TEARSINHEAVEN | 13 | 1993 Song of the Year Grammy winner (3 wds.) |
| 49% | MARYJ | 5 | "Mudbound" actress ___ Blige: 2 wds. |
| 49% | FOOLFORYOU | 10 | Best R&B Song Grammy winner for 39-Across: 3 wds. |
| 49% | MEGHANTRAINOR | 13 | Winner of the 2016 Best New Artist Grammy: 2 wds. |
| 49% | JUNECARTERCASH | 14 | "Ring of Fire" songwriter and five-time Grammy winner whose first name is a month of the year (2 wds.) |
| 48% | REBAMCENTIRE | 12 | "Sing It Now: Songs of Faith & Hope" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 48% | DIANAKRALL | 10 | "When I Look in Your Eyes" Best Jazz Vocal Album Grammy winner who was born on November 16, 1964 (2 wds.) |
| 47% | STAPLETON | 9 | Grammy winner Chris whose album "From a Room: Volume 2" was released on December 1 |
| 47% | TEARSINHEAVEN | 13 | Song of the Year Grammy winner (1993) sung by Eric Clapton (3 wds.) |
| 47% | FROMADISTANCE | 13 | Song of the Year Grammy winner (1991) sung by Bette Midler (3 wds.) |
| 47% | MARIAHCAREY | 11 | Five-time Grammy winner who is the only artist whose first five singles reached #1 on the Billboard Hot 100 (2 wds.) |
| 45% | ANAHEIMDUCKS | 12 | 2007 Stanley Cup winners: 2 wds. |
| 45% | BOSTONBRUINS | 12 | 2011 Stanley Cup winners: 2 wds. |
| 45% | LITTLEBIGTOWN | 13 | Winner of the 2016 Grammy for Best Country Duo/Group Performance: 3 wds. |
| 43% | ONEA | 4 | "Every ___ winner!": 2 wds. |
| 42% | JIMMYCONNORS | 12 | Wimbledon winner in 1974: 2 wds. |