| 100% | ENYA | 4 | One-named singer who has won four Best New Age Album Grammys |
| 95% | ENYA | 4 | One-named Irish singer who has won four Best New Age Album Grammys |
| 53% | ENYA | 4 | Singer who won a Best New Age Album Grammy Award for "Amarantine" |
| 51% | ENYA | 4 | Irish singer who has won four Grammys |
| 45% | ENYA | 4 | New Age vocalist who has won four Grammy Awards |
| 45% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 45% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 41% | ADELE | 5 | One-named singer whose four studio albums have numerical titles |
| 41% | VICTORIAMONET | 13 | "On My Mama" R&B singer who won Best New Artist at the 2024 Grammys: 2 wds. |
| 41% | ADELE | 5 | British singer who has won 15 Grammys since 2009 |
| 41% | STEVIEWONDER | 12 | "Superstition" singer who has won 25 Grammys: 2 wds. |
| 40% | ADELE | 5 | One-named singer who won Grammys for "25" and 14-Across |
| 40% | ADELE | 5 | One-named singer who won the 2016 Album of the Year |
| 40% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 39% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 39% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 39% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 39% | 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. |
| 38% | ENYA | 4 | Four-time Best New Age Album Grammy winner |
| 38% | ALISONKRAUSS | 12 | "When You Say Nothing at All" country singer who has won 27 Grammys: 2 wds. |
| 38% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 37% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 37% | JOHNHANES | 9 | American engineer/mixer who has won the Grammy thrice for "Best Album of the Year," including one for "24k Magic": 2 wds. |
| 37% | CARTER | 6 | Jimmy ___, US President who has won three Grammy awards for Best Spoken Word Album |
| 37% | BARACK | 6 | ___ Obama, US President who has won two Grammy awards for Best Spoken Word Album |
| 37% | FRANKSINATRA | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "September of My Years": 2 wds. |
| 37% | PAULSIMON | 9 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Bridge over Troubled Water": 2 wds. |
| 37% | CYNDI | 5 | Singer Lauper who has won an Emmy, a Tony, and two Grammys |
| 36% | ADELE | 5 | Female artist other than Beyonce who has won the most Grammys in one night, with 6 |
| 36% | DANGELO | 7 | One-named R&B singer who won a Grammy for his 2014 album "Black Messiah" |