| Winner in a landslide in 1972 | 29 |
| Winner in a well-known upset | 28 |
| Winner in Zaire, 10/30/74 | 25 |
| Winner of 11 Oscars in 1997 | 27 |
| Winner of 12 batting titles | 27 |
| Winner of 17 electoral votes | 28 |
| Winner of 1968 and 1972 | 23 |
| Winner of 200 NASCAR races | 26 |
| Winner of 324 baseball games | 28 |
| Winner of 49 Pulitzer Prizes | 28 |
| Winner of 81 PGA tournaments | 28 |
| Winner of 82 PGA Tour events | 28 |
| Winner of 82 PGA tournaments | 28 |
| Winner of a 1944 Pulitzer | 25 |
| Winner of a sci-fi award? | 25 |
| Winner of all four majors | 25 |
| Winner of back-to-back Oscars | 29 |
| Winner of five 1965 Oscars | 26 |
| Winner of five dogfights | 24 |
| Winner of nine 2011 Tonys | 25 |
| Winner of nine Emmys in 1977 | 28 |
| Winner of nine golf majors | 26 |
| Winner of seven Emmy awards | 27 |
| Winner of seven French Opens | 28 |
| Winner of seven Tonys in 1980 | 29 |
| Winner of six Grammys in 2012 | 29 |
| Winner of six U.S. Opens | 24 |
| Winner of the 1968 U.S. Open | 28 |
| Winner of the first FedEx Cup | 29 |
| Winner of the Yom Kippur War | 28 |
| Winner of three Masters | 23 |
| Winner of two Triple Crowns | 27 |
| Winner over Alexander in 1804 | 29 |
| Winner over B.M.G.: 1964 | 24 |
| Winner over Ford: 1976 | 22 |
| Winner over Foreman in Zaire | 28 |
| Winner over R.A.T. in 1952 | 26 |
| Winner over Schmeling in 1938 | 29 |
| Winner over T.E.D.: 1948 | 24 |
| Winner when heads loses | 23 |
| Winner's amount, perhaps | 28 |
| Winner's circle circle | 26 |
| Winner's kind of day | 24 |
| Winner's medal metal | 24 |
| Winner's privilege | 22 |
| Winner's prize, perhaps | 27 |
| Winner's reward: arch. | 26 |
| Winner's take, at times | 27 |
| Winner's take, often | 24 |
| Winner's take, sometimes | 28 |
| Winner-take-all contest | 23 |
| WinnerÂ’s slangy boast | 25 |
| Winners have the fewest | 23 |
| Winners of a certain TV show | 28 |
| Winners of five dogfights | 25 |
| Winners of Super Bowl I | 23 |
| Winners of Super Bowl III | 25 |
| Winners of Super Bowl XXXI | 26 |
| Winners of Super Bowl XXXIV | 27 |
| Winners when led in no-trump | 28 |
| Winners' opposites | 22 |
| Winnie the Pooh author | 25 |
| Winnie the Pooh creator | 26 |
| Winnie the Pooh, for one | 24 |
| Winnie Winkle of comics | 23 |
| Winnie Winkle of comics, e.g. | 29 |
| Winnie ___ (famous plane) | 25 |
| Winnie's husband once | 25 |
| Winnie-the-Pooh catchphrase | 27 |
| Winnie-the-Pooh receptacle | 26 |
| Winnie-the-Pooh's creator | 29 |
| Winnie-the-Pooh, for one | 24 |
| Winning 2004 team, for short | 28 |
| Winning big, Vegas-style | 24 |
| Winning bird's sound? | 25 |
| Winning blackjack combo | 23 |
| Winning blackjack holding | 25 |
| Winning by a single point | 25 |
| Winning by a small margin | 25 |
| Winning card, in bridge | 23 |
| Winning craps roll, in Rome | 27 |
| Winning cry in a card game | 26 |
| Winning edges, frequently | 25 |
| Winning full house, for short | 29 |
| Winning general in 1945 | 23 |
| Winning hand in blackjack | 25 |
| Winning hand's winnings | 27 |
| Winning hit, in baseball | 24 |
| Winning horse's take | 24 |
| Winning it all at a casino | 26 |
| Winning line in tic-tac-toe | 27 |
| Winning margin at a track | 25 |
| Winning margin, at times | 24 |
| Winning margin, perhaps | 23 |
| Winning margin, sometimes | 25 |
| Winning or losing follower | 26 |
| Winning or losing series | 24 |
| Winning over by persistence | 27 |
| Winning owner's party | 25 |
| Winning row in tic-tac-toe | 26 |