| Winning game line | 17 |
| Winning full house, for short | 29 |
| Winning flex for Mr. Universe? | 30 |
| Winning finish? | 15 |
| Winning feeling | 15 |
| Winning edges, frequently | 25 |
| Winning cry in a card game | 26 |
| Winning craps roll, in Rome | 27 |
| Winning come-out rolls in craps | 31 |
| Winning combo on "Hollywood Squares" | 46 |
| Winning coach: 1970 Super Bowl | 30 |
| Winning coach of the first two Super Bowls | 42 |
| Winning coach of Super Bowl IV | 30 |
| Winning coach in Super Bowl XX | 30 |
| Winning coach in Super Bowl IV | 30 |
| Winning coach at the first two Super Bowls | 42 |
| Winning coach at the 2008 Final Four | 36 |
| Winning coach at Super Bowl XII | 31 |
| Winning chess matches | 21 |
| Winning cards | 13 |
| 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 |