| Winning score in darts | 22 |
| Winning service in tennis | 25 |
| Winning slot machine numbers | 28 |
| Winning smile, for one | 22 |
| Winning smile, they say | 23 |
| Winning streak, so to speak | 27 |
| Winning stroke in tennis | 24 |
| Winning team's plaudit | 26 |
| Winning the jackpot, e.g. | 25 |
| Winning the lottery, say | 24 |
| Winning the lottery, usually | 28 |
| Winning tic-tac-toe line | 24 |
| Winning tic-tac-toe row | 23 |
| Winning tic-tac-toe sequence | 28 |
| Winning, but not by much | 24 |
| Winning, for the moment | 23 |
| Winning-everything connector | 28 |
| Winning-everything link | 23 |
| Winningest baseball manager | 27 |
| Winningest baseball southpaw | 28 |
| Winningest lefthanded pitcher | 29 |
| Winnings, to a gambler | 22 |
| Winnipeg actress, Deanna | 24 |
| Winnipeg is its capital | 23 |
| Winnipeg white lightning | 24 |
| Winnipeg's Neil ____ | 24 |
| Winnipeg's province | 23 |
| Winnipeg-to-Memphis dir. | 24 |
| Wino's bad times: abbr. | 27 |
| Wino's visions, for short | 29 |
| Winona of Reality Bites | 27 |
| Winona and Mitch, e.g. | 22 |
| Winona in a halter top? | 23 |
| Winona of 'Heathers' | 28 |
| Wins a certain card game | 24 |
| Wins a hollering contest | 24 |
| Wins at a certain card game | 27 |
| Wins at cards, perhaps | 22 |
| Wins big on poker night | 23 |
| Wins big, with "up" | 29 |
| Wins every game in a series | 27 |
| Wins the draw, probably | 23 |
| Wins the strongman contest | 26 |
| Winslet of 'Titanic' | 28 |
| Winslow Homer painting | 22 |
| Winslow Homer specialty | 23 |
| Winslow Homer's home | 24 |
| Winslow ___, U.S. artist | 24 |
| Winsor McCay character | 22 |
| Winsor McCay comic strip | 24 |
| Winston Churchill flashed it | 28 |
| Winston Churchill, e.g. | 23 |
| Winter 1997-98 newsmaker | 24 |
| Winter aid for windshields | 26 |
| Winter ailment, informally | 26 |
| Winter angler's device | 26 |
| Winter autobahn hazard | 22 |
| Winter begins with one | 22 |
| Winter bird attracters | 22 |
| Winter bird feeder food | 23 |
| Winter blackout cause, often | 28 |
| Winter blanket material | 23 |
| Winter break, of a sort | 23 |
| Winter buildup, at times | 24 |
| Winter carnival attraction | 26 |
| Winter carnival frequenters? | 28 |
| Winter carnival structure | 25 |
| Winter celebration in Vietnam | 29 |
| Winter Chi. clock setting | 25 |
| Winter climber's need | 25 |
| Winter climber's tool | 25 |
| Winter clock setting at LAX | 27 |
| Winter clock setting at MIT | 27 |
| Winter clock setting in L.A. | 28 |
| Winter clock setting in Nev. | 28 |
| Winter clock setting in NJ | 26 |
| Winter clock setting in S.F. | 28 |
| Winter clock setting in Vt. | 27 |
| Winter coat in France? | 22 |
| Winter cry in New York | 22 |
| Winter delivery, for many | 25 |
| Winter driveway clearer | 23 |
| Winter driveway clearers | 24 |
| Winter driving hazards | 22 |
| Winter driving impairment | 25 |
| Winter driving necessities | 26 |
| Winter driving quartet | 22 |
| Winter engine necessity | 23 |
| Winter face-protectors | 22 |
| Winter fall, in ad-speak | 24 |
| Winter fall, in Falkirk | 23 |
| Winter falls, old style | 23 |
| Winter fender bender cause | 26 |
| Winter fender-bender cause | 26 |
| Winter fisherman's access | 29 |
| Winter fisherman's tool | 27 |
| Winter follower (abbr.) | 23 |
| Winter follower: Abbr. | 22 |
| Winter forecast, sometimes | 26 |
| Winter Games competitions | 25 |