| Wind ... cruise ... canvas | 26 |
| Wind (up) | 9 |
| Wind (prefix) | 13 |
| Wind to Juan | 13 |
| Wind of a sort | 15 |
| Wind for one | 13 |
| Wind | 4 |
| Winchman | 8 |
| Winchesters, e.g. | 17 |
| Winchester, for one | 19 |
| Winchester, e.g. | 16 |
| Winchester's saint | 22 |
| Winchester's rank on "M*A*S*H" | 44 |
| Winchester's "MASH" rank | 38 |
| Winchester wielders | 19 |
| Winchester weight | 17 |
| Winchester weapon | 17 |
| Winchester product | 18 |
| Winchester or Springfield | 25 |
| Winchester | 10 |
| Winches | 7 |
| Winchell, for one | 17 |
| Winchell's Orange Juice Gulch | 33 |
| Winchell's dummy sidekick | 29 |
| Winch on an oil-well rig | 24 |
| Winces | 6 |
| Wince, say | 10 |
| Wince, for instance | 19 |
| Wince, e.g. | 11 |
| Wince or flinch, e.g. | 21 |
| Wince or flinch | 15 |
| Wince | 5 |
| Winans with multiple Grammy Awards | 34 |
| Winans who sang a duet with Whitney Houston | 43 |
| Winans who sang "Addictive Love" with her brother | 59 |
| Winans of gospel | 16 |
| Win. follow-up | 14 |
| Win-win transaction | 19 |
| Win-win solutions | 17 |
| Win-or-lose auction offer | 25 |
| Win-lose propositions | 21 |
| Win-and-place wager | 19 |
| Win, WWF style | 14 |
| Win, at an auction | 18 |
| Win, as rewards | 15 |
| Win, as a job | 13 |
| Win's opposite | 18 |
| Win ___, former radio emcee | 27 |
| Win ___ walk | 12 |
| Win ___ nose | 12 |
| Win ___ | 7 |
| Win __, lose ... | 16 |
| Win __ nose | 11 |
| Win __ hair | 11 |
| Win worth celebrating | 21 |
| Win without losing once | 23 |
| Win with ease | 13 |
| Win with difficulty | 19 |
| Win whose money, in a bygone game show? | 39 |
| Win while wrestling | 19 |
| Win when one isn't expected to | 34 |
| Win unexpectedly | 16 |
| Win three of three | 18 |
| Win them all | 12 |
| Win the World Series without a loss | 35 |
| Win the World Series in four games, say | 39 |
| Win the support of | 18 |
| Win the series in four | 22 |
| Win the pie contest | 19 |
| Win the love of | 15 |
| Win the lottery? | 16 |
| Win the lottery, say | 20 |
| Win the lottery, e.g. | 21 |
| Win the jackpot | 15 |
| Win the Home Run Derby, e.g. | 28 |
| Win the heart of | 16 |
| Win the gold | 12 |
| Win the first four World Series games | 37 |
| Win the first four games in a World Series, e.g. | 48 |
| Win the favor of | 16 |
| Win the debate with | 19 |
| Win the confidence of | 21 |
| Win the bread | 13 |
| Win that wasnÂ’t worth it | 28 |
| Win that brings little actual gain | 34 |
| Win over, romantically | 22 |
| Win over with flattery | 22 |
| Win over by persuasion | 22 |
| Win over by persistence | 23 |
| Win over | 8 |
| Win out | 7 |
| Win offset by losses | 20 |
| Win more than a jackpot | 23 |
| Win margin | 10 |
| Win it all | 10 |
| Win in ___ (triumph easily) | 27 |
| Win in ___ (breeze to victory) | 30 |
| Win in jousting | 15 |
| Win in an upset | 15 |
| Win in a walk | 13 |