| 100% | ANOSE | 5 | Win by ___ (horseracing term): 2 wds. |
| 65% | ANOSE | 5 | Win by ___ (barely be victorious): 2 wds. |
| 65% | ANOSE | 5 | Win by ___ (barely take first place): 2 wds. |
| 64% | ANOSE | 5 | Win by ___ (win by a narrow margin): 2 wds. |
| 62% | ANOSE | 5 | Win by ___ (barely beat) (2 wds.) |
| 60% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 60% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 60% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 60% | TONYAWARD | 9 | 2005 Broadway honor won by 15-Across: 2 wds. |
| 60% | STANLEYCUP | 10 | Large silver trophy won by the Penguins: 2 wds. |
| 59% | BESTACTOR | 9 | Oscar won by 21-Across for "The King's Speech": 2 wds. |
| 59% | KENTUCKYDERBY | 13 | May 4 horse race won by Orb: 2 wds. |
| 58% | CORPUSCHRISTI | 13 | "Miss ___," the title won by 18a before she moved to Hollywood: 2 wds. |
| 58% | ILOST | 5 | "___ fair and square" ("They won by fair means."): 2 wds |
| 58% | UPONE | 5 | Winning by a small margin (2 wds.) |
| 57% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 57% | PULITZERPRIZE | 13 | Prestigious award for authors, won by 42-Across for her first novel: 2 wds. |
| 57% | UPONE | 5 | Winning by a very small margin (2 wds.) |
| 57% | GOLDMEDAL | 9 | Olympic prize won by Pat Summitt as coach of the 1984 US team: 2 wds. |
| 56% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 56% | ACADEMYAWARDS | 13 | Golden statuettes won by 15- and 26-/34-Across during a February 22 ceremony: 2 wds. |
| 54% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 54% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 53% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 52% | BARTOLOCOLON | 12 | Dominican pitcher who, last August, set the record for most wins by a Latin American pitcher with 246: 2 wds. |
| 49% | INERROR | 7 | By mistake: 2 wds. |
| 49% | ALLALONE | 8 | By oneself: 2 wds. |
| 48% | BESTDIRECTOR | 12 | Oscar won four times by John Ford: 2 wds. |
| 48% | ALLSTARGAME | 11 | Annual mid-season MLB event won by the American League 4-3 in 2019 (2 wds.) |
| 48% | THEMATCH | 8 | 2020 team charity golf event won by 1-Across/55-Across and 15-Across (2 wds.) |