| Winner of 82 PGA Tour events | 28 |
| Winner of 81 PGA tournaments | 28 |
| Winner of 81 P.G.A. Tour victories | 34 |
| Winner of 49 Pulitzer Prizes | 28 |
| Winner of 37 medals at the Vancouver Winter Olympics | 52 |
| Winner of 324 baseball games | 28 |
| Winner of 26 Oscars | 19 |
| Winner of 2009's Best Supporting Actress Oscar for "Precious" | 75 |
| Winner of 2008 | 14 |
| Winner of 200 NASCAR races | 26 |
| Winner of 2.7% of the 2000 presidential vote | 44 |
| Winner of 1968 and 1972 | 23 |
| Winner of 1948 | 14 |
| Winner of 1865 | 14 |
| Winner of 17 electoral votes | 28 |
| Winner of 16 Grammys | 20 |
| Winner of 159 electoral votes in 1996 | 37 |
| Winner of 14 tennis majors in the 1990s | 39 |
| Winner of 12 NCAA basketball championships | 42 |
| Winner of 12 batting titles | 27 |
| Winner of 11 Oscars in 1997 | 27 |
| Winner of 11 Grand Slam tournament titles | 41 |
| Winner of 101 Pulitzer Prizes: Abbr. | 36 |
| Winner of 100th Kentucky Derby | 30 |
| Winner of 100 NCAA team championships | 37 |
| Winner of 10/30/74 | 18 |
| Winner of 10 tennis Grand Slam singles titles | 45 |
| Winner of "The Thrilla in Manila" | 43 |
| Winner of "Survivor: Cook Islands" | 44 |
| Winner of '82 PGA Anheuser-Busch classic | 44 |
| Winner in Zaire, 10/30/74 | 25 |
| Winner in tennis | 16 |
| Winner in Mailer's "The Fight" | 44 |
| Winner in early Nov. | 20 |
| Winner in blackjack | 19 |
| Winner in an hors d'oeuvres cook-off? | 41 |
| Winner in a well-known upset | 28 |
| Winner in a landslide in 1972 | 29 |
| Winner in a landmark 1973 Supreme Court case | 44 |
| Winner in a famous headline | 27 |
| Winner in a famous 1948 headline | 32 |
| Winner in a fabled upset | 24 |
| Winner in 1954 | 14 |
| Winner in 1876 | 14 |
| Winner between two Pats Super Bowls | 35 |
| Winner before Affirmed | 22 |
| Winner at Wimbledon: 1975 | 25 |
| Winner at Wimbledon: 1925 | 25 |
| Winner at Thermopylae | 21 |
| Winner at the second battle of Bull Run | 39 |
| Winner at the inaugural Latin Grammy Awards | 43 |
| Winner at the Battle of Cold Harbor | 35 |
| Winner at Saratoga: 1777 | 24 |
| Winner at Saratoga | 18 |
| Winner at roulette, often | 25 |
| Winner at roulette | 18 |
| Winner at Oakmont in 1994 | 25 |
| Winner at Madison Square Garden: Sept. 1977 | 43 |
| Winner at Gettysburg | 20 |
| Winner at Chancellorsville | 26 |
| Winner at Caesar's palace? | 30 |
| Winner at Bull Run | 18 |
| Winner at Brandywine | 20 |
| Winner --- | 10 |
| Winner | 6 |
| Winnemucca resident, e.g. | 25 |
| Winnemac, in Sinclair Lewis novels | 34 |
| Winnebagos, for short | 21 |
| Winnebagos, briefly | 19 |
| Winnebagos' kin | 19 |
| Winnebagos e.g. briefly | 25 |
| Winnebago-driving elder? | 24 |
| Winnebago, for one | 18 |
| Winnebago, e.g. | 15 |
| Winnebago's cousin | 22 |
| Winnebago separatists | 21 |
| Winnebago relatives | 19 |
| Winnebago relative | 18 |
| Winnebago owner, for short | 26 |
| Winnebago owner, briefly | 24 |
| Winnebago owner | 15 |
| Winnebago or Cherokee | 21 |
| Winnebago offshoot | 18 |
| Winnebago occupant | 18 |
| Winnebago nation tribe | 22 |
| Winnebago member | 16 |
| Winnebago enthusiast, in the lingo | 34 |
| Winnebago enthusiast, briefly | 29 |
| Winnebago enthusiast | 20 |
| Winnebago driver, informally | 28 |
| Winnebago descendants | 21 |
| Winne ____ Pu | 13 |
| Winless thoroughbred | 20 |
| Winless racehorse | 17 |
| Winless race horse | 18 |
| Winless horses | 14 |
| Winless horse | 13 |
| Winks count | 11 |
| Winks | 5 |
| Winkles out | 11 |