| 100% | BRUNOMARS | 9 | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| 65% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 60% | KACEYMUSGRAVES | 14 | Artist whose album "Golden Hour" won Album of the Year at the 2019 Grammys: 2 wds. |
| 60% | ADELE | 5 | Only performer to twice sweep the Album, Record and Song of the Year Grammys |
| 55% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 54% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 53% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 53% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 53% | FLOWERS | 7 | Miley Cyrus song that won Record of the Year at the 2024 Grammys |
| 51% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 51% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 51% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 51% | FRANKSINATRA | 12 | Actor in the Best Picture winner "From Here to Eternity" who was nominated for seven Album of the Year Grammys: 2 wds. |
| 51% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 51% | ADELE | 5 | Song of the Year winner for "Hello" at the 2017 Grammys |
| 51% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 50% | REHAB | 5 | Song of the Year at the 2008 Grammys |
| 50% | KATIELEDECKY | 12 | Seven-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2013-2018 and 2021 Golden Goggle Awards: 2 wds. |
| 50% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 50% | ADELE | 5 | Record of the Year winner at the 2017 Grammys |
| 50% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 49% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 48% | REHAB | 5 | Amy Winehouse 2008 Grammy Award for Song of the Year and Record of the Year winner |
| 48% | HELLO | 5 | Adele hit that won Grammys for Song and Record of the Year |
| 48% | REHAB | 5 | 2008 Grammy Award for Song of the Year and Record of the Year winner by Amy Winehouse |
| 48% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 48% | ROAR | 4 | Katy Perry song that lost Song of the Year at the 2013 Grammys |
| 47% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 47% | ADELE | 5 | Artist with two Record of the Year and two Album of the Year Grammys |
| 47% | MISSYFRANKLIN | 13 | Five-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2011 and 2012 Golden Goggle Awards: 2 wds. |