| Winnie-the-Pooh's favorite nosh | 35 |
| Winnie-the-Pooh, e.g. | 21 |
| Winnie-the-Pooh, for one | 24 |
| Winnie-the-__ | 13 |
| Winnie-the-___ | 14 |
| Winnie-the-___ House | 20 |
| Winnie-__-Pooh | 14 |
| Winning | 7 |
| Winning "Hollywood Squares" line | 42 |
| Winning "Hollywood Squares" line, at times | 52 |
| Winning 2004 team, for short | 28 |
| Winning 3-2, e.g. | 17 |
| Winning a race | 14 |
| Winning advantage | 17 |
| Winning all the games in a series | 33 |
| Winning an Olympic gold medal, for some | 39 |
| Winning an Oscar, Emmy and Tony, e.g. | 37 |
| Winning and then some | 21 |
| Winning at chess | 16 |
| Winning big | 11 |
| Winning big, Vegas-style | 24 |
| Winning bird colony? | 20 |
| Winning bird's sound? | 25 |
| Winning blackjack combo | 23 |
| Winning blackjack holding | 25 |
| Winning by a point | 18 |
| Winning by a single point | 25 |
| Winning by a small margin | 25 |
| Winning Cagney role | 19 |
| Winning candidate | 17 |
| Winning candidates | 18 |
| Winning card combo | 18 |
| Winning card, in bridge | 23 |
| Winning cards | 13 |
| Winning chess matches | 21 |
| Winning coach at Super Bowl XII | 31 |
| Winning coach at the 2008 Final Four | 36 |
| Winning coach at the first two Super Bowls | 42 |
| Winning coach in Super Bowl IV | 30 |
| Winning coach in Super Bowl XX | 30 |
| Winning coach of Super Bowl IV | 30 |
| Winning coach of the first two Super Bowls | 42 |
| Winning coach: 1970 Super Bowl | 30 |
| Winning combo on "Hollywood Squares" | 46 |
| Winning come-out rolls in craps | 31 |
| Winning craps roll, in Rome | 27 |
| Winning cry in a card game | 26 |
| Winning edges, frequently | 25 |
| Winning feeling | 15 |
| Winning finish? | 15 |
| Winning flex for Mr. Universe? | 30 |
| Winning full house, for short | 29 |
| Winning game line | 17 |
| Winning general in 1945 | 23 |
| Winning gesture | 15 |
| Winning gestures | 16 |
| Winning hand after hand, in poker | 33 |
| Winning hand in blackjack | 25 |
| Winning hand's winnings | 27 |
| Winning hit, in baseball | 24 |
| Winning hit, in baseball argot | 30 |
| Winning hit, in baseball lingo | 30 |
| Winning hit, perhaps | 20 |
| Winning hit: Slang | 18 |
| Winning horse's take | 24 |
| Winning in Vegas | 16 |
| Winning it all at a casino | 26 |
| Winning length in a horse race | 30 |
| Winning like crazy | 18 |
| Winning line in a kids' game | 32 |
| Winning line in tic-tac-toe | 27 |
| Winning line on "Tic Tac Dough" | 41 |
| Winning lineup | 14 |
| Winning manager in 1978 World Series | 36 |
| Winning manager of the 1980 World Series | 40 |
| Winning manager of the 2005 World Series | 40 |
| Winning margin | 14 |
| Winning margin at a track | 25 |
| Winning margin of a horse race, perhaps | 39 |
| Winning margin, at times | 24 |
| Winning margin, maybe | 21 |
| Winning margin, perhaps | 23 |
| Winning margin, sometimes | 25 |
| Winning margin? | 15 |
| Winning margins | 15 |
| Winning move? | 13 |
| Winning nonstop | 15 |
| Winning number | 14 |
| Winning numbers | 15 |
| Winning or losing follower | 26 |
| Winning or losing run | 21 |
| Winning or losing series | 24 |
| Winning over by persistence | 27 |
| Winning owner's party | 25 |
| Winning pennant: 1979 | 21 |
| Winning pianist? | 16 |
| Winning pitcher: 1984 All-Star game | 35 |
| Winning player in Super Bowl XL | 31 |
| Winning player in Super Bowl XXXIV | 34 |
| Winning position | 16 |