| Winner over Ford: 1976 | 22 |
| Winner over B.M.G.: 1964 | 24 |
| Winner over Alexander in 1804 | 29 |
| Winner of two Triple Crowns | 27 |
| Winner of three Masters | 23 |
| Winner of the Yom Kippur War | 28 |
| Winner of the first FedEx Cup | 29 |
| Winner of the 1968 U.S. Open | 28 |
| Winner of six U.S. Opens | 24 |
| Winner of six Grammys in 2012 | 29 |
| Winner of seven Tonys in 1980 | 29 |
| Winner of seven French Opens | 28 |
| Winner of seven Emmy awards | 27 |
| Winner of nine golf majors | 26 |
| Winner of nine Emmys in 1977 | 28 |
| Winner of nine 2011 Tonys | 25 |
| Winner of five dogfights | 24 |
| Winner of five 1965 Oscars | 26 |
| Winner of back-to-back Oscars | 29 |
| Winner of all four majors | 25 |
| Winner of a sci-fi award? | 25 |
| Winner of a 1944 Pulitzer | 25 |
| Winner of 82 PGA tournaments | 28 |
| Winner of 82 PGA Tour events | 28 |
| Winner of 81 PGA tournaments | 28 |
| Winner of 49 Pulitzer Prizes | 28 |
| Winner of 324 baseball games | 28 |
| Winner of 200 NASCAR races | 26 |
| Winner of 1968 and 1972 | 23 |
| Winner of 17 electoral votes | 28 |
| Winner of 12 batting titles | 27 |
| Winner of 11 Oscars in 1997 | 27 |
| Winner in Zaire, 10/30/74 | 25 |
| Winner in a well-known upset | 28 |
| Winner in a landslide in 1972 | 29 |
| Winner in a famous headline | 27 |
| Winner in a fabled upset | 24 |
| Winner before Affirmed | 22 |
| Winner at Wimbledon: 1975 | 25 |
| Winner at Wimbledon: 1925 | 25 |
| Winner at Saratoga: 1777 | 24 |
| Winner at roulette, often | 25 |
| Winner at Oakmont in 1994 | 25 |
| Winner at Chancellorsville | 26 |
| Winnemucca resident, e.g. | 25 |
| Winnebagos e.g. briefly | 25 |
| Winnebago-driving elder? | 24 |
| Winnebago's cousin | 22 |
| Winnebago owner, for short | 26 |
| Winnebago owner, briefly | 24 |
| Winnebago nation tribe | 22 |
| Winnebago enthusiast, briefly | 29 |
| Winnebago driver, informally | 28 |
| Winkle or scope preceder | 24 |
| Winkle or meter preceder | 24 |
| Winker's apparatus | 22 |
| Winken and Blinken partner | 26 |
| Winken and Blinken companion | 28 |
| Wink without batting an eye? | 28 |
| Wink in tiddlywinks, e.g. | 25 |
| Wining and dining place | 23 |
| Wingwalker's vehicle | 24 |
| Wingtips, for instance | 22 |
| Wingtip-to-wingtip dimensions | 29 |
| Wingtip-to-wingtip dimension | 28 |
| Wings, to an entomologist | 25 |
| Wings, anatomically speaking | 28 |
| Wings that don't flap | 25 |
| Wings Neck Lighthouse setting | 29 |
| Wings hit "___ In" | 28 |
| Wings eaters' needs | 23 |
| Wingless, extinct bird | 22 |
| Wingless, bloodsucking insect | 29 |
| Wingless blood-suckers | 22 |
| Winger guitarist Beach | 22 |
| Winged woodland dwellers | 24 |
| Winged wonders of myth | 22 |
| Winged symbol of Venice | 23 |
| Winged statue in the Louvre | 27 |
| Winged or slippery ___ | 22 |
| Winged or slippery trees | 24 |
| Winged one in Wonderland | 24 |
| Winged monster of Greek myth | 28 |
| Winged Greek god with a bow | 27 |
| Winged goddess of victory | 25 |
| Winged fruit of the maple | 25 |
| Winged figure of mythology | 26 |
| Winged clothing consumer | 24 |
| Winged child, in sculpture | 26 |
| Winged celestial being | 22 |
| Winged being, in Germany | 24 |
| Wingding, British style | 23 |
| Wing-to-wing dimensions | 23 |
| Wing-designing calculation | 26 |
| Wing with no feathers? | 22 |
| Wing tip-to-wing tip distance | 29 |
| Wing that can't fly | 23 |
| Wing that can't flap | 24 |
| Wing of a two-family house? | 27 |
| Wing of a building, perhaps | 27 |