| 100% | DEREK | 5 | Teammate of Mariano for 19 years |
| 41% | TEEN | 4 | 13 to 19 years of age |
| 41% | ASA | 3 | King of Judah for 41 years |
| 40% | SEASONAL | 8 | For certain times of the year |
| 39% | 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.) |
| 38% | OSCARS | 6 | Meryl Streep has been nominated for 19 of these awards |
| 38% | WOMAN | 5 | Year of the ___ (moniker for 1992 and 2018) |
| 38% | ELUL | 4 | End of the year, for some |
| 38% | SEASONAL | 8 | Apt for the time of year |
| 38% | YEARNED | 7 | Longed for; anagram of end year |
| 38% | KYRIEIRVING | 11 | Teammate of 41-Across for Cleveland's NBA championship in 2016 (2 wds.) |
| 37% | CENTURIES | 9 | Somehow censure it for hundreds of years |
| 37% | OCT | 3 | Time of year for much raking: Abbr. |
| 37% | DEC | 3 | End of the year month, for short |
| 37% | PST | 3 | Ore. setting for part of the year |
| 37% | APR | 3 | Fourth month of the year, for short |
| 37% | MAR | 3 | Third month of the year, for short |
| 37% | SEP | 3 | Ninth month of the year, for short |
| 37% | AUG | 3 | Eighth month of the year, for short |
| 37% | SEM | 3 | Segment of a school year, for short |
| 37% | AGED | 4 | Like Scotch, for a minimum of three years |
| 37% | GIULIANI | 8 | Time's Person of the Year for 2001 |
| 37% | CLIO | 4 | Award for Agency of the Year, e.g. |
| 37% | ADELE | 5 | Billboard's Artist of the Year for 2011 |
| 37% | RAZZIE | 6 | Award for the worst movie of the year |
| 37% | ADELE | 5 | 2017 Song of the Year winner for "Hello" |
| 37% | LTM | 3 | Finance abbreviation used for duration of last year |
| 37% | ALMANAC | 7 | Annual publication for events of the coming year |
| 37% | INDIGIRKA | 9 | Siberian river frozen for half of the year |
| 37% | DWYANEWADE | 10 | Teammate of 41-Across for Miami's NBA championships in 2012 and 2013 (2 wds.) |