| Wine-drinking occasion | 22 |
| Wine-flavored espagnole | 23 |
| Wine-flavored Italian ice | 25 |
| Wine-honey-spice drink | 22 |
| Wine-lover's prefix | 23 |
| Wine-producing city of note | 27 |
| Wine-producing province | 23 |
| Wine-tasters' routines | 26 |
| Wine-tasting accessory | 22 |
| Wine-tasting consideration | 26 |
| Wined and dined, perhaps | 24 |
| Winegrowing region of France | 28 |
| Winehouse grammy winner | 23 |
| Winemaker Ernest or Julio | 25 |
| Winemaker's sediment | 24 |
| Winemaker's valley | 22 |
| Winemakers Ernest and Julio | 27 |
| Winemaking province of Italy | 28 |
| Winery in Modesto, Calif. | 25 |
| Winery in Sonoma County | 23 |
| Winery surname of fame | 22 |
| Wines and dines, for example | 28 |
| Wines that aren't whites | 28 |
| Wines that go with steaks | 25 |
| Wines to serve with beef | 24 |
| Wines with steaks, usually | 26 |
| Winesap or Northern Spy | 23 |
| Winesap or wineglass feature | 28 |
| Winetaster's asset | 22 |
| Winetaster's concern | 24 |
| Winetaster's criterion | 26 |
| Winfield of the Yankees | 23 |
| Winfrey of 'Beloved' | 28 |
| Winfrey's inspiration | 25 |
| Wing commander's org. | 25 |
| Wing of a building, perhaps | 27 |
| Wing of a two-family house? | 27 |
| Wing that can't flap | 24 |
| Wing that can't fly | 23 |
| Wing tip-to-wing tip distance | 29 |
| Wing with no feathers? | 22 |
| Wing-designing calculation | 26 |
| Wing-to-wing dimensions | 23 |
| Wingding, British style | 23 |
| Winged being, in Germany | 24 |
| Winged celestial being | 22 |
| Winged child, in sculpture | 26 |
| Winged clothing consumer | 24 |
| Winged figure of mythology | 26 |
| Winged fruit of the maple | 25 |
| Winged goddess of victory | 25 |
| Winged Greek god with a bow | 27 |
| Winged monster of Greek myth | 28 |
| Winged one in Wonderland | 24 |
| Winged or slippery trees | 24 |
| Winged or slippery ___ | 22 |
| Winged statue in the Louvre | 27 |
| Winged symbol of Venice | 23 |
| Winged wonders of myth | 22 |
| Winged woodland dwellers | 24 |
| Winger guitarist Beach | 22 |
| Wingless blood-suckers | 22 |
| Wingless, bloodsucking insect | 29 |
| Wingless, extinct bird | 22 |
| Wings eaters' needs | 23 |
| Wings hit "___ In" | 28 |
| Wings Neck Lighthouse setting | 29 |
| Wings that don't flap | 25 |
| Wings, anatomically speaking | 28 |
| Wings, to an entomologist | 25 |
| Wingtip-to-wingtip dimension | 28 |
| Wingtip-to-wingtip dimensions | 29 |
| Wingtips, for instance | 22 |
| Wingwalker's vehicle | 24 |
| Wining and dining place | 23 |
| Wink in tiddlywinks, e.g. | 25 |
| Wink without batting an eye? | 28 |
| Winken and Blinken companion | 28 |
| Winken and Blinken partner | 26 |
| Winker's apparatus | 22 |
| Winkle or meter preceder | 24 |
| Winkle or scope preceder | 24 |
| Winnebago driver, informally | 28 |
| Winnebago enthusiast, briefly | 29 |
| Winnebago nation tribe | 22 |
| Winnebago owner, briefly | 24 |
| Winnebago owner, for short | 26 |
| Winnebago's cousin | 22 |
| Winnebago-driving elder? | 24 |
| Winnebagos e.g. briefly | 25 |
| Winnemucca resident, e.g. | 25 |
| Winner at Chancellorsville | 26 |
| Winner at Oakmont in 1994 | 25 |
| Winner at roulette, often | 25 |
| Winner at Saratoga: 1777 | 24 |
| Winner at Wimbledon: 1925 | 25 |
| Winner at Wimbledon: 1975 | 25 |
| Winner before Affirmed | 22 |
| Winner in a fabled upset | 24 |
| Winner in a famous headline | 27 |