| 100% | TIMEFLIES | 9 | "The years just whiz by!": 2 wds. |
| 61% | ONEBC | 5 | Year just before the AD period began: 2 wds. |
| 54% | ALLYEAR | 7 | ___ round (throughout the year): 2 wds. |
| 52% | KEVINDURANT | 11 | NBA MVP in the year 2014: 2 wds. |
| 51% | VIVALAVIDA | 10 | 2009 Grammy Song of the Year by Coldplay: 3 wds. |
| 51% | ARIANAGRANDE | 12 | Singer recently named Breakthrough Artist of the Year by the Music Business Association: 2 wds. |
| 50% | NEEDYOUNOW | 10 | 2011 Grammy Song of the Year by Lady Antebellum: 3 wds. |
| 50% | STEELYDAN | 9 | "Reelin' in the Years" yacht rock band: 2 wds. |
| 50% | TIMEFLIES | 9 | "The years just zip by!" |
| 50% | WINELABEL | 9 | Bottle wrapper that displays the year of your burgundy, say: 2 wds. |
| 50% | BENBERNANKE | 11 | Economist who was Time's 2009 Person of the Year: 2 wds. |
| 49% | TEARSINHEAVEN | 13 | Song of the Year Grammy winner (1993) sung by Eric Clapton (3 wds.) |
| 49% | FROMADISTANCE | 13 | Song of the Year Grammy winner (1991) sung by Bette Midler (3 wds.) |
| 49% | VLADIMIRPUTIN | 13 | Russian leader who was Time's 2007 Person of the Year: 2 wds. |
| 49% | DONALDTRUMP | 11 | US leader who was Time's 2016 Person of the Year: 2 wds. |
| 49% | POPEFRANCIS | 11 | Vatican leader who was Time's 2013 Person of the Year: 2 wds. |
| 49% | DREWBREES | 9 | Quarterback who was Sports Illustrated's 2010 Sportsman of the Year: 2 wds. |
| 49% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 49% | GRETATHUNBERG | 13 | Teen activist who was Time's 2019 Person of the Year: 2 wds. |
| 49% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 49% | STEPHONCASTLE | 13 | San Antonio Spurs guard named 2025 NBA Rookie of the Year: 2 wds. |
| 48% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 48% | JALENBRUNSON | 12 | New York Knicks guard named 2025 NBA Clutch Player of the Year: 2 wds. |
| 48% | LIONELMESSI | 11 | Inter Miami captain who was Time's 2023 Athlete of the Year: 2 wds. |
| 48% | CAITLINCLARK | 12 | Indiana Fever player who was Time's 2024 Athlete of the Year: 2 wds. |
| 47% | BRUNOMARS | 9 | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| 47% | THETERMINATOR | 13 | Time traveler sent to kill or protect Sarah Connor (depending on the year): 2 wds. |
| 47% | ARIANAGRANDE | 12 | "Thank U, Next" singer recognized as Billboard's 2018 Woman of the Year: 2 wds. |
| 47% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 47% | SIMONEBILES | 11 | Most decorated American gymnast who was Time's 2021 Athlete of the Year: 2 wds. |