| 100% | ROSANNECASH | 11 | "Seven Year Ache" country singer born May 24, 1955 (2 wds.) |
| 86% | ROSANNECASH | 11 | "Seven Year Ache" singer born May 24, 1955 (2 wds.) |
| 50% | TAMMYWYNETTE | 12 | "Stand by Your Man" country singer born May 5, 1942 (2 wds.) |
| 50% | WYNONNAJUDD | 11 | "I Saw the Light" country singer born May 30, 1964 (2 wds.) |
| 41% | ZACHBRYAN | 9 | "Something in the Orange" country singer who served eight years in the Navy: 2 wds. |
| 41% | JAMEYJOHNSON | 12 | "In Color" country singer who served four years in the Marine Corps Reserve: 2 wds. |
| 41% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 41% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 41% | JAMESOTTO | 9 | "Just Got Started Lovin' You" country singer who served two years in the Navy: 2 wds. |
| 41% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer born May 5, 1942 (2 wds.) |
| 41% | WYNONNAJUDD | 11 | "I Saw the Light" singer born May 30, 1964 (2 wds.) |
| 40% | JOEDIFFIE | 9 | "Pickup Man" country singer born in Tulsa, Oklahoma (2 wds.) |
| 40% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 39% | JENNIFERLOPEZ | 13 | Singer/actress born July 24, 1969 (2 wds.) |
| 38% | HOYTAXTON | 9 | "Joy to the World" country singer born in Duncan, Oklahoma (2 wds.) |
| 37% | VINCEGILL | 9 | "I Still Believe in You" country singer born in Norman, Oklahoma (2 wds.) |
| 37% | RICKYSKAGGS | 11 | "Highways & Heartaches" country singer who turned 70 years old on July 18, 2024 (2 wds.) |
| 37% | VINCEGILL | 9 | Country singer who's married to singer Amy Grant: 2 wds. |
| 37% | FAITHHILL | 9 | Country singer who's married to singer Tim McGraw: 2 wds. |
| 37% | KEITHURBAN | 10 | Country singer who's married to actress Nicole Kidman: 2 wds. |
| 37% | BLAKESHELTON | 12 | Country singer and judge on "The Voice": 2 wds. |
| 36% | TOBYKEITH | 9 | "How Do You Like Me Now?!" country singer born in Clinton, Oklahoma (2 wds.) |
| 36% | POSTMALONE | 10 | "Circles" singer born on the Fourth of July, 1995: 2 wds. |
| 36% | KACEYMUSGRAVES | 14 | "Rainbow" country singer recognized as Billboard's 2018 Innovator: 2 wds. |
| 36% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 35% | TIMMCGRAW | 9 | Country singer who collapsed from dehydration while onstage in Dublin: 2 wds. |
| 35% | REBAMCENTIRE | 12 | Country music superstar born March 28, 1955 (2 wds.) |
| 35% | EVERYSTORM | 10 | 2012 hit song from country singer Gary Allan: 2 wds. |
| 35% | KEITHURBAN | 10 | Country singer who was an "American Idol" judge for four seasons: 2 wds. |
| 35% | CHRISTIANKANE | 13 | Country singer who portrays an art/architecture expert on 15-Across: 2 wds. |