| 100% | DEFEAT | 6 | To beat or win over someone in a contest |
| 41% | UNDERDOG | 8 | Someone expected to lose a contest or battle |
| 40% | PARTYFOUL | 9 | Knocking over someone's drink, e.g. … or, homophonically, a hint to 17-, 27-, 39- and 54-Across |
| 39% | RACE | 4 | Change a word in this phrase to correct it! "Slow and steady wins the contest" |
| 39% | WOO | 3 | To win over someone, romantically |
| 38% | FINALISTS | 9 | The last competitors in a contest or tournament |
| 38% | OVERTOOK | 8 | Passed someone in a race, or while driving |
| 38% | OUTFOXING | 9 | Beating someone in a battle of wits |
| 37% | ALSORAN | 7 | Loser in a race or contest |
| 37% | DOLLARSANDCENTS | 15 | Money ... or a hint to how six crossings in this puzzle are to be represented, superimposing one letter over another |
| 37% | WOO | 3 | Try to win over someone |
| 37% | WOO | 3 | Attempt to win over someone |
| 37% | OUTEATS | 7 | Beats in a pie contest? |
| 36% | DEFEAT | 6 | To beat an opponent; a loss in a sporting event |
| 36% | MEDICALLY | 9 | In a way related to treatment of illness or injury |
| 36% | WOO | 3 | Try to win over someone, romantically |
| 36% | HAYSTACK | 8 | Needle in a __, or something difficult to find |
| 36% | OUTEAT | 6 | Beat in a Nathan's contest |
| 36% | OUTEAT | 6 | Beat in a pie contest, say |
| 36% | OUTEAT | 6 | Beat in a hot dog contest |
| 36% | DISOBEY | 7 | To defy someone or a command |
| 36% | YOUSWEAR | 8 | Something done on a stack of Bibles or in response to someone stealing the cheesecake you were going to eat for breakfast |
| 36% | DEAR | 4 | Starting word in a letter to someone you love |
| 36% | FUNHOUSE | 8 | Building in a funfair made to startle or amuse |
| 36% | SELECT | 6 | To choose something or someone over others |
| 36% | BELIEVE | 7 | To have faith in someone or something |
| 36% | HATE | 4 | To dislike something or someone a lot |
| 36% | ENSLAVE | 7 | To make someone or something a drudger |
| 36% | AID | 3 | To lend a hand, or rescue someone. |
| 36% | ADMONISH | 8 | To caution or give someone a warning |