| 100% | OBIE | 4 | Three-time award for David Mamet |
| 74% | OBIE | 4 | 1983 award for David Mamet |
| 63% | EDGAR | 5 | Award for Best Novel won three times by Dick Francis |
| 57% | MVP | 3 | Three-time award for Berra, for short |
| 55% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 54% | OBIES | 5 | Awards for Mamet |
| 53% | MVP | 3 | Three-time AL award for Mantle |
| 52% | TBSP | 4 | Three times 49a, for short |
| 49% | LOREN | 5 | Record six-time David di Donatello Award winner for Best Actress |
| 47% | PEDROMARTINEZ | 13 | Three-time Cy Young Award winner who debuted as a TV analyst for the 2013 playoffs: 2 wds. |
| 47% | BYE | 3 | When said three times, hit song for 46-Down |
| 46% | RHO | 3 | When said three times, good name for a crew fraternity? |
| 46% | TONY | 4 | Award that "Hamilton" is nominated for 16 times |
| 46% | DENY | 4 | When said three times, mantra for some accused |
| 45% | CYYOUNG | 7 | Award named for the winningest pitcher of all time |
| 45% | SHELDON | 7 | This Cooper knocks three times, asks for Penny |
| 45% | RELATION | 8 | Your second cousin, three times removed, for one |
| 45% | OSCAR | 5 | Award won three times by Meryl Streep |
| 44% | EMMY | 4 | Award Julia Louis-Dreyfus has won for three different roles |
| 44% | EMMY | 4 | Award Bryan Cranston won four times for portraying Walter White |
| 44% | GLAM | 4 | Rock genre of David Bowie, for a time |
| 44% | MVP | 3 | Four-time award for LeBron James |
| 44% | TREBLE | 6 | Register for three times as much |
| 43% | PITT | 4 | Brad ___ who won an Academy Award for "Once Upon a Time in Hollywood" |
| 43% | MEDIA | 5 | Subject for late New York Times columnist David Carr |
| 43% | SIGOURNEYWEAVER | 15 | Three-time Academy Award nominee |
| 43% | ELIA | 4 | Three-time director for Marlon |
| 43% | NEO | 3 | Three-time role for Keanu |
| 43% | MRTIBBS | 7 | Three-time role for Poitier |
| 43% | ALI | 3 | Three-time foe for Frazier |