| Wins big, with "up" | 29 |
| Wins big on poker night | 23 |
| Wins big in Vegas | 17 |
| Wins big | 8 |
| Wins back | 9 |
| Wins at the board | 17 |
| Wins at chess | 13 |
| Wins at cards, perhaps | 22 |
| Wins at a certain card game | 27 |
| Wins approval | 13 |
| Wins an advantage | 17 |
| Wins affection | 14 |
| Wins acceptance | 15 |
| Wins a race easily | 18 |
| Wins a hollering contest | 24 |
| Wins a fight | 12 |
| Wins a dispute | 14 |
| Wins a chess match | 18 |
| Wins a certain card game | 24 |
| Wins a card game | 16 |
| Wins a bridge hand? | 19 |
| Wins a board game | 17 |
| Wins $199,000 on "Jeopardy!," say | 43 |
| Wins | 4 |
| Winos, etc. | 11 |
| Winos | 5 |
| Winooski River city | 19 |
| Winona's role in "Great Balls of Fire!" | 53 |
| Winona's "Beetlejuice" role | 41 |
| Winona who was the V.P. on Nader's presidential ticket | 58 |
| Winona the actress | 18 |
| Winona of Hollywood | 19 |
| Winona of films | 15 |
| Winona of "Mermaids" | 30 |
| Winona of "Girl, Interrupted" | 39 |
| Winona of "Edward Scissorhands" | 41 |
| Winona of "Black Swan" | 32 |
| Winona of "Beetlejuice" | 33 |
| Winona of 'Heathers' | 28 |
| Winona nominated for Razzie awards in 2001 and 2003 | 51 |
| Winona in a halter top? | 23 |
| Winona from Winona | 18 |
| Winona and Mitch, e.g. | 22 |
| Winona the actress | 19 |
| Winona of Reality Bites | 27 |
| Winold ___, painter of Indians | 30 |
| Wino's woes | 15 |
| Wino's woe | 14 |
| Wino's visions, for short | 29 |
| Wino's visions | 18 |
| Wino's trademark | 20 |
| Wino's blood type? (straight pun) | 37 |
| Wino's bad times: abbr. | 27 |
| Wino's ailment | 18 |
| Wino's affliction | 21 |
| Wino | 4 |
| Winnows | 7 |
| Winnowing waste | 15 |
| WINNOWING or ERECT | 18 |
| Winnowing device | 16 |
| Winnowed | 8 |
| Winnow | 6 |
| Winnipeg-to-Memphis dir. | 24 |
| Winnipeg's ___ Franko Museum | 32 |
| Winnipeg's river | 20 |
| Winnipeg's province | 23 |
| Winnipeg's Neil ____ | 24 |
| Winnipeg's ____ Garry Hotel | 32 |
| Winnipeg winter hrs. | 20 |
| Winnipeg white lightning | 24 |
| Winnipeg time | 13 |
| Winnipeg swindle? | 17 |
| Winnipeg suburb | 15 |
| Winnipeg or Ontario | 19 |
| Winnipeg main drag | 18 |
| Winnipeg is its capital | 23 |
| Winnipeg goalie moonlighting as a mercenary? | 44 |
| Winnipeg Free Press car-toonist | 31 |
| Winnipeg area | 13 |
| Winnipeg airport ID | 19 |
| Winnipeg actress, Deanna | 24 |
| Winnings, to a gambler | 22 |
| Winnings | 8 |
| Winningly youthful | 18 |
| Winningest southpaw in major-league history | 43 |
| Winningest NFL coach | 20 |
| Winningest NCAA basketball coach until 1997 | 43 |
| Winningest nat. in the Summer Olympics | 38 |
| Winningest N.C.A.A. basketball coach | 36 |
| Winningest Montreal Expos manager | 33 |
| Winningest manager in Expos history | 35 |
| Winningest lefty | 16 |
| Winningest lefthanded pitcher | 29 |
| Winningest left-handed pitcher | 30 |
| Winningest knuckleballer of all-time | 36 |
| Winningest club in the UEFA Champions League | 44 |
| Winningest baseball southpaw | 28 |
| Winningest baseball manager | 27 |
| Winning-everything link | 23 |
| Winning-everything connector | 28 |