| Winning smile, e.g. | 19 |
| Winning smile, for one | 22 |
| Winning smile, great personality and the like | 45 |
| Winning smile, they say | 23 |
| Winning spell | 13 |
| Winning steadily | 16 |
| Winning streak | 14 |
| Winning streak, so to speak | 27 |
| Winning stroke in tennis | 24 |
| Winning Super Bowl III coach Ewbank | 35 |
| Winning Super Bowl III quarterback | 34 |
| Winning Super Bowl XVIII player | 31 |
| Winning Super Bowl XXXIV player | 31 |
| Winning Super Bowl XXXVII gridder | 33 |
| Winning symbols | 15 |
| Winning team in the Pine Tar Incident | 37 |
| Winning team's plaudit | 26 |
| Winning tennis serves | 21 |
| Winning the jackpot, e.g. | 25 |
| Winning the lottery, say | 24 |
| Winning the lottery, usually | 28 |
| Winning the Powerball jackpot, for example | 42 |
| Winning the race | 16 |
| Winning tic-tac-toe line | 24 |
| Winning tic-tac-toe row | 23 |
| Winning tic-tac-toe sequence | 28 |
| Winning trio? | 13 |
| Winning two pair hand | 21 |
| Winning way | 11 |
| Winning word at the 1984 National Spelling Bee | 46 |
| Winning words | 13 |
| Winning words? | 14 |
| Winning X | 9 |
| Winning X or O | 14 |
| Winning, barely | 15 |
| Winning, but barely | 19 |
| Winning, but not by much | 24 |
| Winning, for now | 16 |
| Winning, for the moment | 23 |
| Winning-everything connector | 28 |
| Winning-everything link | 23 |
| Winningest baseball manager | 27 |
| Winningest baseball southpaw | 28 |
| Winningest club in the UEFA Champions League | 44 |
| Winningest knuckleballer of all-time | 36 |
| Winningest left-handed pitcher | 30 |
| Winningest lefthanded pitcher | 29 |
| Winningest lefty | 16 |
| Winningest manager in Expos history | 35 |
| Winningest Montreal Expos manager | 33 |
| Winningest N.C.A.A. basketball coach | 36 |
| Winningest nat. in the Summer Olympics | 38 |
| Winningest NCAA basketball coach until 1997 | 43 |
| Winningest NFL coach | 20 |
| Winningest southpaw in major-league history | 43 |
| Winningly youthful | 18 |
| Winnings | 8 |
| Winnings, to a gambler | 22 |
| Winnipeg actress, Deanna | 24 |
| Winnipeg airport ID | 19 |
| Winnipeg area | 13 |
| Winnipeg Free Press car-toonist | 31 |
| Winnipeg goalie moonlighting as a mercenary? | 44 |
| Winnipeg is its capital | 23 |
| Winnipeg main drag | 18 |
| Winnipeg or Ontario | 19 |
| Winnipeg suburb | 15 |
| Winnipeg swindle? | 17 |
| Winnipeg time | 13 |
| Winnipeg white lightning | 24 |
| Winnipeg winter hrs. | 20 |
| Winnipeg's ____ Garry Hotel | 32 |
| Winnipeg's Neil ____ | 24 |
| Winnipeg's province | 23 |
| Winnipeg's river | 20 |
| Winnipeg's ___ Franko Museum | 32 |
| Winnipeg-to-Memphis dir. | 24 |
| Winnow | 6 |
| Winnowed | 8 |
| Winnowing device | 16 |
| WINNOWING or ERECT | 18 |
| Winnowing waste | 15 |
| Winnows | 7 |
| Wino | 4 |
| Wino's affliction | 21 |
| Wino's ailment | 18 |
| Wino's bad times: abbr. | 27 |
| Wino's blood type? (straight pun) | 37 |
| Wino's trademark | 20 |
| Wino's visions | 18 |
| Wino's visions, for short | 29 |
| Wino's woe | 14 |
| Wino's woes | 15 |
| Winold ___, painter of Indians | 30 |
| Winona of Reality Bites | 27 |
| Winona the actress | 19 |
| Winona and Mitch, e.g. | 22 |
| Winona from Winona | 18 |
| Winona in a halter top? | 23 |
| Winona nominated for Razzie awards in 2001 and 2003 | 51 |