| Winning card, in bridge | 23 |
| Winning card combo | 18 |
| Winning candidates | 18 |
| Winning candidate | 17 |
| Winning Cagney role | 19 |
| Winning by a small margin | 25 |
| Winning by a single point | 25 |
| Winning by a point | 18 |
| Winning blackjack holding | 25 |
| Winning blackjack combo | 23 |
| Winning bird's sound? | 25 |
| Winning bird colony? | 20 |
| Winning big, Vegas-style | 24 |
| Winning big | 11 |
| Winning at chess | 16 |
| Winning and then some | 21 |
| Winning an Oscar, Emmy and Tony, e.g. | 37 |
| Winning an Olympic gold medal, for some | 39 |
| Winning all the games in a series | 33 |
| Winning advantage | 17 |
| Winning a race | 14 |
| Winning 3-2, e.g. | 17 |
| Winning 2004 team, for short | 28 |
| Winning "Hollywood Squares" line, at times | 52 |
| Winning "Hollywood Squares" line | 42 |
| Winning | 7 |
| Winnie-__-Pooh | 14 |
| Winnie-the-___ House | 20 |
| Winnie-the-___ | 14 |
| Winnie-the-__ | 13 |
| Winnie-the-Pooh, for one | 24 |
| Winnie-the-Pooh, e.g. | 21 |
| Winnie-the-Pooh's favorite nosh | 35 |
| Winnie-the-Pooh's favorite food | 35 |
| Winnie-the-Pooh's donkey friend | 35 |
| Winnie-the-Pooh's creator | 29 |
| Winnie-the-Pooh receptacle | 26 |
| Winnie-the-Pooh possession / Baked entree / Sweetie | 51 |
| Winnie-the-Pooh catchphrase | 27 |
| Winnie-the- ____ | 16 |
| Winnie's title? | 19 |
| Winnie's sign | 17 |
| Winnie's husband once | 25 |
| Winnie's creator | 20 |
| Winnie ____ Pu | 14 |
| Winnie ___ (Wiley Post's plane) | 35 |
| Winnie ___ (famous plane) | 25 |
| Winnie Winkle of comics, e.g. | 29 |
| Winnie Winkle of comics | 23 |
| Winnie the ____ | 15 |
| Winnie the ___ | 14 |
| Winnie the __ | 13 |
| Winnie the Pooh, for one | 24 |
| Winnie the Pooh pal | 19 |
| Winnie the Pooh creator's monogram | 38 |
| Winnie the Pooh creator | 26 |
| Winnie the Pooh author | 25 |
| Winnie the Pooh | 15 |
| Winnie or Smokey | 16 |
| Winnie of fiction | 17 |
| Winnie Mae pilot | 16 |
| Winnie -- Pooh | 14 |
| Winnie | 6 |
| Winners' takes | 18 |
| Winners' signs | 18 |
| Winners' opposites | 22 |
| Winners' gestures | 21 |
| Winners' flashes | 20 |
| Winners' euphoria | 21 |
| Winners' checks? | 20 |
| Winners when led in no-trump | 28 |
| Winners on the courts | 21 |
| Winners of the second World Series | 34 |
| Winners of the longest postseason game in major-league history (18 innings, 2005) | 81 |
| Winners of the first Super Bowl | 31 |
| Winners of the 2013-14 Premiership, for short | 45 |
| Winners of Super Bowls XXXII and XXXIII | 39 |
| Winners of Super Bowl XXXIV | 27 |
| Winners of Super Bowl XXXI | 26 |
| Winners of Super Bowl III | 25 |
| Winners of Super Bowl I | 23 |
| Winners of some televised singing competitions | 46 |
| Winners of five dogfights | 25 |
| Winners of a certain TV show | 28 |
| Winners in 1918 | 15 |
| Winners have the fewest | 23 |
| Winners get them | 16 |
| Winners can be determined by one | 32 |
| Winners break it | 16 |
| Winners at the polls | 20 |
| Winners | 7 |
| Winnerless game | 15 |
| WinnerÂ’s slangy boast | 25 |
| WinnerÂ’s look | 17 |
| Winner-take-all playground game | 31 |
| Winner-take-all contest | 23 |
| Winner, with Tippi and Ursula, of the 1963 female New Star of the Year Golden Globe | 83 |
| Winner, usually | 15 |
| Winner, for sure | 16 |
| Winner, claimed the 11/3/48 Chicago Tribune | 43 |