| Text | Length |
| Winston Cup entry | 17 |
| Winston competitor | 18 |
| Winsor heroine | 14 |
| Winslow, the artist | 19 |
| Winslow Homer, e.g. | 19 |
| Winslet or Hudson | 17 |
| Winslet or Capshaw | 18 |
| Winslet and Smith | 17 |
| Winslet and Capshaw | 19 |
| Wins, in a way | 14 |
| Wins, barely | 12 |
| Wins, at an auction | 19 |
| Wins, as a contract | 19 |
| Wins the favor of | 17 |
| Wins support from | 17 |
| Wins recognition | 16 |
| Wins one, loses one | 19 |
| Wins in a walkover | 18 |
| Wins in a card game | 19 |
| Wins going away | 15 |
| Wins everything | 15 |
| Wins every game of | 18 |
| Wins by a nose | 14 |
| Wins big in Vegas | 17 |
| Wins at the board | 17 |
| Wins at chess | 13 |
| Wins approval | 13 |
| Wins an advantage | 17 |
| Wins affection | 14 |
| Wins acceptance | 15 |
| Wins a race easily | 18 |
| Wins a fight | 12 |
| Wins a dispute | 14 |
| Wins a chess match | 18 |
| Wins a card game | 16 |
| Wins a bridge hand? | 19 |
| Wins a board game | 17 |
| Winooski River city | 19 |
| Winona the actress | 18 |
| Winona of Hollywood | 19 |
| Winona of films | 15 |
| Winona from Winona | 18 |
| Winona the actress | 19 |
| Wino's woes | 15 |
| Wino's woe | 14 |
| Wino's visions | 18 |
| Wino's ailment | 18 |
| Winnowing waste | 15 |
| WINNOWING or ERECT | 18 |
| Winnowing device | 16 |
| Winnipeg time | 13 |
| Winnipeg swindle? | 17 |
| Winnipeg suburb | 15 |
| Winnipeg or Ontario | 19 |
| Winnipeg main drag | 18 |
| Winnipeg area | 13 |
| Winnipeg airport ID | 19 |
| Winningly youthful | 18 |
| Winningest lefty | 16 |
| Winning, for now | 16 |
| Winning, but barely | 19 |
| Winning, barely | 15 |
| Winning X or O | 14 |
| Winning words? | 14 |
| Winning words | 13 |
| Winning trio? | 13 |
| Winning the race | 16 |
| Winning symbols | 15 |
| Winning streak | 14 |
| Winning steadily | 16 |
| Winning spell | 13 |
| Winning smile, e.g. | 19 |
| Winning signs | 13 |
| Winning sign | 12 |
| Winning show dog? | 17 |
| Winning serve | 13 |
| Winning sequence | 16 |
| Winning position | 16 |
| Winning pianist? | 16 |
| Winning numbers | 15 |
| Winning number | 14 |
| Winning nonstop | 15 |
| Winning move? | 13 |
| Winning margins | 15 |
| Winning margin? | 15 |
| Winning margin | 14 |
| Winning lineup | 14 |
| Winning like crazy | 18 |
| Winning in Vegas | 16 |
| Winning hit: Slang | 18 |
| Winning gestures | 16 |
| Winning gesture | 15 |
| Winning game line | 17 |
| Winning finish? | 15 |
| Winning feeling | 15 |
| Winning cards | 13 |
| Winning card combo | 18 |
| Winning candidates | 18 |
| Winning candidate | 17 |
| Winning Cagney role | 19 |
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