- Winner in a fabled upset
- Winner in a famous headline
- Winner in a landslide in 1972
- Winner in a well-known upset
- winner in examination for university teaching post
- Winner in Tennis
- winner Indy 500 1983 winner
- winner James Pulitzer 1934 writer
- winner Jones Grammy 1988 winner
- winner Judith Tony
- winner Kentucky Derby 1984 winner
- winner Lewis Emmy
- winner Loretta Emmy
- winner Lucci Emmy
- winner Luyendyk Indy 500 1983 winner
- winner Masters 1996 winner
- winner Neuwirth Tony
- winner November birthstone
- Winner of 10/30/74
- Winner of 11 Grand Slam tennis titles
- Winner of 11 Grand Slam tournament titles
- Winner of 11 Oscars in 1997
- Winner of 11 Tonys in 2016
- Winner of 11 World Series, for short
- Winner of 13 Outstanding Drama Series Emmys
- Winner of 14 tennis majors in the 1990s
- Winner of 15 Grammys (2009-2017)
- Winner of 159 electoral votes in 1996
- Winner of 18 Grand Slam tennis titles from 1936 to 1940
- Winner of 1865
- Winner of 1948
- Winner of 1968 and 1972
- Winner of 1971 Nobel prize for literature
- Winner of 2.7% of the 2000 presidential vote
- Winner of 2008
- Winner of 22 Grand Slam singles titles, second-most in the Open Era
- Winner of 3 consecutive U.S. Opens
- Winner of 324 baseball games
- Winner of 33 Daytime Emmys
- Winner of 37 medals at the Vancouver Winter Olympics
- Winner of 46 gold medals at the Rio Olympics
- Winner of 49 Pulitzer Prizes
- Winner of 8 Grammys in 1999
- Winner of 81 P.G.A. Tour victories
- Winner of 81 PGA tournaments
- Winner of 82 PGA Tour events
- Winner of 82 PGA Tour tournaments
- Winner of 82 PGA tournaments
- Winner of a 1925 intercollegiate crossword championship
- Winner of a 1944 Pulitzer
- Winner of a 1960 Grammy with Lawrence
- Winner of a 1970s-'80s war
- Winner of a career Grand Slam in tennis
- Winner of a Down East pageant
- Winner of a famous 1938 rematch
- Winner of a Fox talent show beginning in 2002
- Winner of a landmark 1966 Supreme Court decision
- winner of a medal
- Winner of a popular TV talent show
- Winner of a posthumous Pulitzer
- Winner of a posthumous Pulitzer for "A Death in the Family"
- Winner of a race
- Winner of a record 82 P.G.A. Tour events
- Winner of a record 82 PGA tournaments
- Winner of a record eight N.H.L. Norris Trophies
- Winner of a sci-fi award?
- Winner of a sprint
- Winner of a Tony and an Oscar for the same role
- Winner of a TV talent show
- Winner of acting, writing and directing Emmys from a single series
- Winner of all four Grand Slam singles events in tennis
- Winner of all four grand slam titles
- Winner of all four majors
- Winner of all four majors in tennis
- Winner of all three tug-of-war medals in the 1904 Olympics: Abbr.
- Winner of an Emmy, a Grammy, an Oscar, and three Golden Globes
- Winner of an Indianapolis race, e.g.
- Winner of at least one Grand Slam event every year from 1974 to 1986
- Winner of back-to-back Best Rock Instrumental Grammys in 1980 and 1981
- Winner of back-to-back Oscars
- Winner of dual Worst Actress Razzies for "I Know Who Killed Me"
- Winner of eight choreography Tonys
- Winner of eight gold medals in 2008
- Winner of eight Grand Slam titles as a teen
- Winner of eight Grand Slam tournaments
- Winner of eight Norris Trophies
- Winner of five 2015 Primetime Emmys
- Winner of five consecutive Wimbledons
- Winner of five gold medals at the '88 Olympics
- Winner of five gold medals at the 1980 Winter Olympics
- Winner of five golds at Lake Placid
- Winner of four 1990s-2000s golf majors
- Winner of four 1996 Tony Awards
- Winner of four consecutive Olympic gold medals
- Winner of four consecutive U.S. Open titles
- Winner of four FIFA World Cups
- Winner of four gold medals at the Berlin Olympics
- Winner of four gold medals in 1936
- Winner of four Indy 500s
- Winner of four New Age Grammys
- Winner of four Outstanding Comedy Series Emmys
- Winner of four straight U.S. Opens, 1975-'78
- Winner of four World Series in this century, on scoreboards
- Winner of more than half of all the World Puzzle Championships
- winner of most tennis grand slams
- Winner of nine golf majors
- Winner of nine Grand Slam titles
- Winner of nine Grand Slam tournaments in the 1990s
- Winner of over 125 Pulitzer Prizes, for short
- winner of prize
- Winner of seven Emmys
- Winner of seven French Opens
- Winner of seven straight NCAA hoops championships
- Winner of seven tennis majors in the 1920s
- Winner of seven Tonys
- Winner of seven Tonys in 1977
- Winner of seven Tonys in 1980
- Winner of seven Wimbledons
- Winner of six 2011 Grammys
- Winner of six David di Donatello acting awards
- Winner of six Grammys in 2012
- Winner of six Grand Slam men's singles titles from 1985 to 1992
- Winner of six Teen Choice Awards, 1999-2003
- Winner of six U.S. Opens
- Winner of some Olympic competitions
- Winner of Super Bowls VII and VIII
- Winner of Superbowl III
- Winner of tennis's Grand Slam in 1962 and 1969
- Winner of the "Thrilla in Manila"
- Winner of the 1942 Masters
- Winner of the 1966 World Cup: Abbr
- Winner of the 1968 U.S. Open
- Winner of the 1970 Hart Trophy, Conn Smythe Trophy, Norris Trophy, and Art Ross Trophy
- Winner of the 1976 ABA Slam Dunk contest
- Winner of the 1976 Pulitzer Prize for Music
- Winner of the 1985 Best New Artist Grammy
- Winner of the 1997 and 1998 Super Bowls
- Winner of the 1999 Best Foreign Language Film Oscar
- Winner of the 2000 Golden Globe for Best Director
- Winner of the 2005 and 2007 Grammys for Best Spoken Word Album
- Winner of the 2005 Best Picture Oscar
- Winner of the 2006 Orange Bowl
- Winner of the first FedEx Cup
- Winner of the first French Open
- Winner of the first slam dunk contest
- Winner of the first Super Bowl
- Winner of the first three Fiesta Bowls, for short
- Winner of the first two Super Bowl MVPs
- Winner of the first World Cup: Abbr.
- Winner of the first World Series (as the "Americans")
- Winner of the four tennis majors and Olympic 8-Down
- Winner of the inaugural College Football Playoff
- Winner of the lowest-scoring Super Bowl in N.F.L. history (16 total points)
- Winner of the most 2016 Olympic medals
- Winner of the most French Open singles titles
- Winner of the most Grand Slam singles titles in the Open Era
- Winner of the most medals at the 2018 Winter Olympics: Abbr.
- Winner of the most medals at the 2020 Olympics
- Winner of the most singles titles
- Winner of the most Women's World Cups
- Winner of the Olympics 2010
- Winner of the wager in 17-/56-Across, depending on how you fill the circled squares in this puzzle
- Winner of three consecutive Emmys for "Mission: Impossible"
- Winner of three Grand Slam events
- Winner of three Masters
- Winner of three of 2000's four majors
- Winner of three Oscars in 2013
- Winner of three Pulitzer Prizes for Drama
- Winner of three Wimbledons
- Winner of two Grammys and a Nobel Peace Prize
- Winner of two Oscars and two Tonys
- Winner of two U.S., three French, and four Australian Opens
- Winner of Wimbledon for five consecutive years
- winner Oscar
- Winner over Alexander in 1804
- Winner over NYY in the 2001 World Series
- Winner over Ohio State in 1935's so-called "Game of the Century"
- Winner over Schmeling in 1938
- Winner over the Patriots in Super Bowl XXXI
- winner Pageant accessory
- winner Preakness
- winner Pulitzer 1934 writer
- winner Pyle Pulitzer 1934 writer
- winner Race
- winner Rivera Tony
- winner Safin U.S. Open 1955 winner
- winner Scott Newbery Medal winner Lowry
- winner Styne Tony
- winner Surefire
- winner Susan Emmy
- winner Swoosie Tony
- winner Thompson Emmy
- winner Tony
- winner Triple Crown 1930 jockey
- winner U.S. Open 1955 winner
- winner Uta Tony
- winner Ward Emmy
- winner Welty Pulitzer 1934 writer
- Winner when heads loses
- Winner who finished next to last, in fable
- Winner winner chicken dinner!
- winner World Cup 1958 sensation
- winner Worth Tony
- Winner-take-all playground game
- Winner, claimed the 11/3/48 Chicago Tribune
- Winner, for short
- Winner, for sure
- Winner, ideally
- Winner, informally
- Winner, usually
- Winner!
- Winner's accessory
- Winner's attitude
- Winner's boast
- Winner's check?
- Winner's crown
- winner's cry
- Winner's cry in a card game
- Winner's demand
- Winner's emotion
- Winner's feeling
- Winner's flag
- Winner's gathering
- Winner's gesture
- Winner's hand gesture
- Winner's haul
- Winner's look
- Winner's material
- Winner's medal metal
- Winner's medalla
- Winner's number
- Winner's overhead gesture
- Winner's pair?
- Winner's poor sportsmanship
- Winner's position
- Winner's privilege
- Winner's prize
- Winner's prize in a programming competition?
- Winner's prize on "RuPaul's Drag U"
- Winner's prize, in 20-Across
- Winner's prize, perhaps
- Winner's sign
- Winner's signs
- Winner's spot
- Winner's take
- Winner's take, often
- Winner's take, perhaps
- Winner's take, sometimes
- Winner's take?
- Winner's token