| Wins a certain card game | 24 |
| Winona of 'Heathers' | 28 |
| Winona in a halter top? | 23 |
| Winona and Mitch, e.g. | 22 |
| Winona of Reality Bites | 27 |
| Wino's visions, for short | 29 |
| Wino's bad times: abbr. | 27 |
| Winnipeg-to-Memphis dir. | 24 |
| Winnipeg's province | 23 |
| Winnipeg's Neil ____ | 24 |
| Winnipeg white lightning | 24 |
| Winnipeg is its capital | 23 |
| Winnipeg actress, Deanna | 24 |
| Winnings, to a gambler | 22 |
| Winningest lefthanded pitcher | 29 |
| Winningest baseball southpaw | 28 |
| Winningest baseball manager | 27 |
| Winning-everything link | 23 |
| Winning-everything connector | 28 |
| Winning, for the moment | 23 |
| Winning, but not by much | 24 |
| Winning tic-tac-toe sequence | 28 |
| Winning tic-tac-toe row | 23 |
| Winning tic-tac-toe line | 24 |
| Winning the lottery, usually | 28 |
| Winning the lottery, say | 24 |
| Winning the jackpot, e.g. | 25 |
| Winning team's plaudit | 26 |
| Winning stroke in tennis | 24 |
| Winning streak, so to speak | 27 |
| Winning smile, they say | 23 |
| Winning smile, for one | 22 |
| Winning slot machine numbers | 28 |
| Winning service in tennis | 25 |
| Winning score in darts | 22 |
| Winning row in tic-tac-toe | 26 |
| Winning owner's party | 25 |
| Winning over by persistence | 27 |
| Winning or losing series | 24 |
| Winning or losing follower | 26 |
| Winning margin, sometimes | 25 |
| Winning margin, perhaps | 23 |
| Winning margin, at times | 24 |
| Winning margin at a track | 25 |
| Winning line in tic-tac-toe | 27 |
| Winning it all at a casino | 26 |
| Winning horse's take | 24 |
| Winning hit, in baseball | 24 |
| Winning hand's winnings | 27 |
| Winning hand in blackjack | 25 |
| Winning general in 1945 | 23 |
| Winning full house, for short | 29 |
| Winning edges, frequently | 25 |
| Winning cry in a card game | 26 |
| Winning craps roll, in Rome | 27 |
| Winning card, in bridge | 23 |
| Winning by a small margin | 25 |
| Winning by a single point | 25 |
| Winning blackjack holding | 25 |
| Winning blackjack combo | 23 |
| Winning bird's sound? | 25 |
| Winning big, Vegas-style | 24 |
| Winning 2004 team, for short | 28 |
| Winnie-the-Pooh, for one | 24 |
| Winnie-the-Pooh's creator | 29 |
| Winnie-the-Pooh receptacle | 26 |
| Winnie-the-Pooh catchphrase | 27 |
| Winnie's husband once | 25 |
| Winnie ___ (famous plane) | 25 |
| Winnie Winkle of comics, e.g. | 29 |
| Winnie Winkle of comics | 23 |
| Winnie the Pooh, for one | 24 |
| Winnie the Pooh creator | 26 |
| Winnie the Pooh author | 25 |
| Winners' opposites | 22 |
| Winners when led in no-trump | 28 |
| 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 five dogfights | 25 |
| Winners of a certain TV show | 28 |
| Winners have the fewest | 23 |
| WinnerÂ’s slangy boast | 25 |
| Winner-take-all contest | 23 |
| Winner's take, sometimes | 28 |
| Winner's take, often | 24 |
| Winner's take, at times | 27 |
| Winner's reward: arch. | 26 |
| Winner's prize, perhaps | 27 |
| Winner's privilege | 22 |
| Winner's medal metal | 24 |
| Winner's kind of day | 24 |
| Winner's circle circle | 26 |
| Winner's amount, perhaps | 28 |
| Winner when heads loses | 23 |
| Winner over T.E.D.: 1948 | 24 |
| Winner over Schmeling in 1938 | 29 |
| Winner over R.A.T. in 1952 | 26 |
| Winner over Foreman in Zaire | 28 |