| 100% | KEB | 3 | ___ Mo', three-time Grammy-winning bluesman |
| 59% | CARR | 4 | Three-time Grammy-winning singer Vikki |
| 58% | CARPENTERS | 10 | Three-time Grammy-winning group with "The" |
| 52% | BESTRAPALBUM | 12 | Grammy category won five times by Eminem |
| 51% | BESTRAPPERFORMANCE | 18 | Grammy category won multiple times by Kendrick Lamar |
| 49% | EARLE | 5 | Three-time Grammy winner Steve |
| 49% | LOU | 3 | Three-time Grammy winner Rawls |
| 49% | DUA | 3 | Three-time Grammy winner ___ Lipa |
| 49% | PENTATONIX | 10 | Three-time Grammy-winning a cappella group that got its start on "The Sing-Off" in 2011 |
| 49% | HELLO | 5 | Adele hit song that won three Grammy Awards |
| 49% | HELLO | 5 | 2015 Adele song that won three Grammy Awards |
| 48% | VAI | 3 | Steven Siro ___, three-time Grammy-winning American guitarist who was born on June 6, 1960 |
| 47% | OSCAR | 5 | Award won three times by Meryl Streep |
| 47% | OSCAR | 5 | Statuette won three times by Meryl Streep |
| 46% | OSCAR | 5 | Statuette won three times by Daniel Day-Lewis |
| 46% | SEAL | 4 | Singer who won three Grammy Awards for "Kiss from a Rose" |
| 46% | REHAB | 5 | 2006 Amy Winehouse hit that won three Grammy Awards in 2008 |
| 46% | RAITT | 5 | She won three Grammys for her 1989 album "Nick of Time" |
| 45% | YANKOVIC | 8 | "Weird Al" ___, comedian who won three Grammy awards for his comedy albums |
| 45% | ROCK | 4 | Chris ___, comedian who has won three Grammy Awards for his comedy albums |
| 45% | DIARY | 5 | "The ___ of Alicia Keys" (R&B album that won three Grammy Awards) |
| 44% | SYSTEMOFADOWN | 13 | Grammy-winning metal band, or what can be found three times in this puzzle? |
| 44% | EVERT | 5 | Chris who won Wimbledon three times |
| 43% | THRICE | 6 | Three times |
| 43% | TRIPLE | 6 | Three times |
| 43% | TRIPLY | 6 | Three times |
| 43% | ALJARREAU | 9 | Singer who won Grammy Awards in three different categories (jazz, pop, and R. & B.) |
| 43% | BRANDI | 6 | ___ Carlile, "Broken Horses" female singer who won three Grammys at the 2023 Grammy Awards |
| 43% | CARTER | 6 | Jimmy ___, US President who has won three Grammy awards for Best Spoken Word Album |
| 43% | NINE | 4 | Three times three |