Wikipedia talk:Manual of Style/List of winningest citations

This is a list of citations and quotations relating to the usage of the word 'winningest'. I'm putting them over here to avoid making a protracted discussion page even larger and more unweildy. Most of these sources are offline or paywalled, but should be accepted per WP:AGF. I encourage everyone to take advantage of the Wikipedia:Reference desk and Wikipedia:The Wikipedia Library for further access and verification. Your local public libraries are very likely to also offer you access to these and many other paywalled resources. Thank you to User:Cbl62 for major expansion of this list. --Dennis Bratland (talk) 22:11, 15 January 2016 (UTC)[reply]

Style guides

Fowler's Concise Dictionary of Modern English Usage (First Edition)

[1]

"Many adjectives besides those described in 1 & 2 are capable of ordinary use, i.e. without the stylistic taint illustrated in 5 & 6, of forming a superlative in -est, used with the & serving as an emphatic form simply, while no-one would think of making a comparative in -er from them: in the brutalist, civilest, timidest, winningest, cogentest, cheerfullest, cunningest, doggiest, drunkenest, candidest, damnablest, manner. The terminations that most invite this treatment are -ful, -ing, -able, -ed, & -id; on the other hand the very common adjective terminations -ive, -ic ,& -ous, reject it altogether (curiouser & curiouser is a product of Wonderland). Though it is hard to draw a clear line between this use & the next, the intent is different; the words are felt to be little less normal & yet appreciably more forcible, than the forms with most; they are superlatives only, & emphasis is their object; an attempt is made to register them in their dictionary places."

Note The passage above also appears in the 1926 First Edition of Fowler's. English in Nineteenth-Century England: An Introduction by Manfred Görlach says that this is an example of Fowler's adherence to 19th Century, rather than modern, usage.

Fowler's Concise Dictionary of Modern English Usage (3 ed.)

Reference type: Subject Reference Current Version: 2015 Subject Language reference, Usage and Grammar Guides

3 comparison.
Adjectives of one or two syllables normally form their comparative and superlative forms by adding -er and -est, sometimes with modification of the stem (soft, softer, softest; happy, happier, happiest). Adjectives of more than two syllables are normally preceded by more or most instead of inflecting (more frightening; most remarkable). For special effect, however, a polysyllabic adjective will sometimes be inflected
('Curiouser and curiouser!' cried Alice —L. Carroll, 1865
One of the generousest creatures alive —Thackeray, 1847/8
The winningest coach in Southwest Conference basketball history —Chicago Tribune, 1990).
See also -er and -est forms of adjectives. Conversely, more and most are sometimes used, for emphasis or special effect, when inflected forms are available: This was never more true than at present / That was the most cruel thing you could have said.

See also a detailed discussion of -er and -est comparative and superlative adjective forms, with several unacceptable or exotic formations discussed, none of which is winningest. [2]

English in Australia

edited by David Blair, Peter Collins [3]

AP Stylebook Online

Ask the Editor
Q. What is the style for "all-time winningest coach/athlete" or "coach/athlete with the most wins all-time?" Is more wordy better in this case? from Mount Pleasant, Iowa on Jun 07, 2014
A. The most wins all-time is preferable. The American Heritage Dictionary lists winningest as an informal adjective.

http://www.apstylebook.com.ezproxy.spl.org:2048/spl_org/?do=search_results&search_term=winningest

H. L. Mencken The American Language

On the question of WP:ENGVAR and WP:TIES. H. L. Mencken discuses the special use of -er and -est adjectives as a peculiarly US American language pattern in The American Language: An Inquiry into the Development of English in the United States. A.A. Knopf, 1921 Chapter: The Common Speech pages 308-309.

7. The Adjective
The adjectives in English are inflected only for comparison, and the American commonly uses them correctly, with now and then a double comparative or superlative to ease his soul. More better is the commonest of these. It has a good deal of support in logic. A sick man is reported today to be better. Tomorrow he is further improved. Is he to be reported better again or best? The standard language gets around the difficulty by using still better. The American vulgate boldly employs more better. In the case of worse, worser is used as Charters shows. He also reports baddest, more queerer and beautifullest. Littler, which he notes, is still outlawed from standard English, but it has, with littlest a respectable place in American. The late Richard Harding Davis wrote a play called "The Littlest Girl" The American freely compares adjectives that are incapable of the inflection logically. Charters reports most principal, and I myself have heard uniquer and even more uniquer, as in "I have never saw nothing more uniquer." I have also heard more ultra, more worse, idealer, liver (that is more alive) and wellest as in "he was the wellest man you ever seen." In general the -er and -est terminations are used instead of the more and most prefixes as in beautiful, beautifuller, beautifullest. The fact that the comparative relates to two and the superlative to more than two is almost always forgotten. I have never heard "the better of the two," in the popular speech but always "the best of the two." Charters also reports "the hardest of the two" and "my brother and I measured and he was the tallest." I have frequently heard "it ain't so worse but here a humorous effect seems to have been intended.

H. L. Mencken

Patricia T. O'Conner On Language columnist, author

Patricia T. O'Conner and Stewart Kellerman, NYT On Language columnist, author of Woe Is I: The Grammarphobe's Guide to Better English in Plain English (Riverhead, 3rd ed., 2010, ISBN 978-1-57322-331-7), Origins of the Specious Myths and Misconceptions of the English Language, The winningest dog November 4th, 2013 and in Is "winningest" a loser? March 6th, 2007. "...it's a legitimate word... the adjective 'winningest' has been around for hundreds of years, first in the sense of most attractive and later in the sporting sense."

Encyclopedias

Britannica

Encyclopædia Britannica

(Britannica Online Reference Center) Author listed if included; not all Brittanica articles mention the author

Bobby Bowden — "Bobby Bowden, in full Robert Cleckler Bowden, (born November 8, 1929, Birmingham, Alabama, U.S.), American collegiate gridiron football coach who was one of the winningest coaches in National Collegiate Athletic Association (NCAA) history." and "pon his retirement, Bowden was second to Paterno in career wins, but he temporarily became the all-time winningest coach in 2012, when the NCAA stripped Paterno of 111 wins as punishment for a years-long sex scandal at his school." Author Adam Augustyn - Manager and Senior Editor, Encyclopædia Britannica.
Martin Brodeur "Martin Brodeur, (born May 6, 1972, Montreal, Quebec, Canada), Canadian ice hockey player who is the all-time winningest goaltender in the National Hockey League (NHL) with 691 career victories." and " In March 2009 Brodeur became the all-time winningest NHL goalie, passing Patrick Roy with his 552nd victory."
New Jersey Devils (American ice hockey team) "Although the Devils continued as one of the NHL's winningest franchises, finishing first or second in the Atlantic Division in each season of the first decade of the 2000s, they failed to return to the Stanley Cup finals that decade."
Wayne Embry (American basketball player and manager) "In 1985 Embry became the general manager...worked with coach Lenny Wilkens to establish the Cavaliers as one of the winningest teams in the NBA in the late '80s " Robert G. Logan - Sportswriter, Chicago Tribune. Author of The Bulls and Chicago: A Stormy Affair.
Phog Allen (American basketball coach) "Conference from 1929 to 1947 and now known as the Big 12). He retired as the winningest coach in college basketball. Regarded as the “father of basketball coaching …"
Greg Maddux (American baseball player) "He retired after the end of the 2008 season with 355 career wins, which made Maddux the second winningest pitcher in baseball's 'live-ball era' (the period that ..."
Sports and recreation from the article Kentucky (state, United States) "Basketball is central to the sports...Adolph Rupp , who guided the team from 1930 to 1972 and was for a long time the winningest coach in the history of college ... " Wilford Allen Bladen - Emeritus Professor of Geography, University of Kentucky, Lexington. Author of Geography of Kentucky and Across the Appalachians. Wilma Dykeman [4] - Adjunct Professor of English, University of Tennessee, Knoxville. State Historian of Tennessee. Author of The French Broad; coauthor of The Appalachian Mountains and others.
Mike Krzyzewski (American basketball coach) "In 2011 he won his 903rd career game to pass Knight as the winningest coach in Division I history. In 2014–15 Duke went 35–4 and captured a fifth national... " Adam Augustyn - Manager and Senior Editor, Encyclopædia Britannica.
St. Louis Cardinals (American baseball team) "Smith's Cardinal teams returned twice more...times. In 1996 the Cardinals hired manager Tony La Russa , who would go on to become the winningest manager in team history." Adam Augustyn - Manager and Senior Editor, Encyclopædia Britannica.
Miami Dolphins (American football team) "Despite experiencing a great deal of...career, a 38–16 loss to the San Francisco 49ers in 1985. Shula retired after the 1995 season as the winningest coach in NFL history."
Montreal Canadiens (Canadian hockey team) "The championship team of 1985–86 featured...and would later retire—after finishing his career with the Colorado Avalanche —as the NHL's winningest goalie of all time."
Bobby Allison (American stock-car racer) "Bobby Allison, byname of Robert Arthur Allison, (born December 3, 1937, Miami, Florida, U.S.), American stock-car racer who was one of the winningest drivers in National Association for Stock Car Auto Racing (NASCAR) history and a member of one of the most notable, and most tragic, families in racing. " Jay Busbee [5] - Sportswriter, Yahoo Sports and NBC Sports Network.
Junior Johnson (American stock-car driver) "Johnson is also credited with inventing...purpose in NASCAR.) Johnson retired in 1966 with 50 Grand National wins, the winningest driver to have never won a..." Jay Busbee - Sportswriter, Yahoo Sports and NBC Sports Network.
Lee Petty (American stock-car driver) "Together with his sons, he established Petty Enterprises, a racing team which would become one of NASCAR's winningest organizations. The team was founded in .. Jay Busbee - Sportswriter, Yahoo Sports and NBC Sports Network.
Jim Palmer (American baseball player) "Palmer was out for most of the 1967 season...season, and problems in the early 1980s led to Baltimore releasing Palmer, their all-time winningest pitcher, in May 1984."
Pat Summitt (American basketball coach) "Summitt, Pat | née Patricia Head (born...women's basketball coach at the University of Tennessee (1974–2012) who was the winningest coach in the history of National..." Amy Tikkanen - Corrections Manager, Encyclopædia Britannica.
Joe Paterno (American football coach) "Paterno, Joe | byname of Joseph...who, as head coach at Pennsylvania State University (1966–2011), was the winningest major-college coach in the history..."
Ole Einar Bjørndalen (Norwegian athlete) "In February 2009, when he captured his 87th World Cup win, he surpassed Swedish alpine skier Ingemar Stenmark as the winningest skier in World Cup history. In ..."
Gunda Niemann-Stirnemann (German athlete) "Her total of eight medals made her one of the winningest athletes in the history of the Winter Games. She retired from competitive skating in 2005. Anthony G. Craine - Independent researcher and writer.

Grolier

Grolier Online Passport

Explore the Encyclopedia Americana, the Grolier Multimedia Encyclopedia, The New Book of Knowledge, Lands and Peoples, and The New Book of Popular Science, and America the Beautiful.

Phelps, Michael (1985– ) American competitive swimmer. "He won 7 gold medals at the 2007 World Championships, making history as the competition's winningest athlete. " Hathaway, Ted. "Phelps, Michael (1985– )." Encyclopedia Americana. Grolier Online, 2016. Web. 15 Jan. 2016.
Martina Navratilova " She eventually became the 'winningest' player in history." "Navratilova, Martina." America the Beautiful. Grolier Online, 2016. Web. 15 Jan. 2016.

Columbia

Columbia Encyclopedia

Some of these are duplicates of Brittanica; others are unique

Bobby Bowden (American football coach) "Bowden, Bobby American football coach in full Robert Cleckler Bowden November 8, 1929 Birmingham, Alabama, U.S. American collegiate gridiron football coach who was one of the winningest coaches ...
New Jersey Devils (American ice hockey team) "Although the Devils continued as one of the NHL’s winningest franchises, finishing first or second in the Atlantic Division in each season of the first decade of the 2000s, they failed to return to the Stanley Cup finals that decade. In 2009 Brodeur recorded his 552nd victory to become the all-time winningest goalie in the NHL. In 2009–10 the Devils topped the 40-win plateau for the 13th consecutive season, matching the record set by the Montreal Canadiens from 1971 to 1983."
Phog Allen (American basketball coach) "He retired as the winningest coach in college basketball."
Miami Dolphins (American football team) "Shula retired after the 1995 season as the winningest coach in NFL history."
Montreal Canadiens (Canadian hockey team) "after finishing his career with the Colorado Avalanche—as the NHL’s winningest goalie of all time."
Gunda Niemann-Stirnemann (German athlete) "Her total of eight medals made her one of the winningest athletes in the history of the Winter Games. She retired from competitive skating in 2005."
Greg Maddux (American baseball player) "He retired after the end of the 2008 season with 355 career wins, which made Maddux the second winningest pitcher in baseball’s “live-ball era” (the period that dates from the introduction of hitter-friendly rules in 1920)."
Sports and recreation from the article Kentucky (state, United States) already quoted
Pat Summitt (American basketball coach) " American collegiate women’s basketball coach at the University of Tennessee (1974–2012) who was the winningest coach in the history of National Collegiate Athletic Association (NCAA) basketball."
St. Louis Cardinals (American baseball team) "In 1996 the Cardinals hired manager Tony La Russa, who would go on to become the winningest manager in team history. "
Defining Dementia: Year In Review 2012 (dementia) "In April 2012, less than a year after having been diagnosed with early-onset dementia, Alzheimer type, American collegiate women’s basketball coach Pat Summitt—the winningest coach in the history of NCAA basketball—retired. "
Sports Roundup for 2012: Year In Review 2012 (sports) "On April 18 the University of Tennessee’s Pat Summitt—the winningest basketball coach in NCAA history, with 1,098 victories—announced that she was stepping down after having been diagnosed with early-onset dementia in 2011. "
Football in 2010 "The Carolina Panthers had the worst record in the NFL (2–14) and at season’s end fired John Fox, the franchise’s winningest coach, who had led the Panthers to their only Super Bowl appearance after the 2003 season."
Joe Paterno (American football coach) "…as head coach at Pennsylvania State University (1966–2011), was the winningest major-college coach in the history of the sport, with 409 career victories, but whose accomplishments were in many ways overshadowed by a sex-abuse scandal that occurred during his tenure."
Ole Einar Bjørndalen (Norwegian athlete) "he surpassed Swedish alpine skier Ingemar Stenmark as the winningest skier in World Cup history. "
Mike Krzyzewski (American basketball coach)
Petty, Lee American stock-car driver March 14, 1914 Randleman, North Carolina "After retiring from racing, Petty turned his energies to the business side of the sport. Together with his sons, he established Petty Enterprises, a racing team which would become one of NASCAR’s winningest organizations. "
Jim Palmer (American baseball player)
Wayne Embry (American basketball player and manager) "and worked with coach Lenny Wilkens to establish the Cavaliers as one of the winningest teams in the NBA in the late ’80s and early ’90s, though they repeatedly fell victim in the play-offs to the great Chicago Bulls teams led by Michael Jordan. "
Kay Yow (American basketball coach)"was a legendary figure in women’s college basketball who served (1975–2009) as the head coach at North Carolina State University and became one of the winningest coaches in National Collegiate Athletic Association (NCAA) Division I history."
Bobby Allison (American stock-car racer) ", American stock-car racer who was one of the winningest drivers in National Association for Stock Car Auto Racing (NASCAR) history and a member "
Junior Johnson (American stock-car driver) "Johnson retired in 1966 with 50 Grand National wins, the winningest driver to have never won a championship, but he began a lucrative and heralded career as a stock-car owner. "

Encyclopaedia Judaica

HOLTZMAN, KENNETH DALE ("Kenny"; 1945– ), "U.S. baseball player, winningest Jewish pitcher in history." Wohlgelernter, Elli. "Holtzman, Kenneth Dale." Encyclopaedia Judaica. Ed. Michael Berenbaum and Fred Skolnik. 2nd ed. Vol. 9. Detroit: Macmillan Reference USA, 2007. 498. Gale Virtual Reference Library. Web. 15 Jan. 2016.

St. James Encyclopedia of Popular Culture

St. James Encyclopedia of Popular Culture Daryl Umberger . Ed. Thomas Riggs . Vol. 4. 2nd ed. Detroit: St. James Press, 2013.

Sports Heroes pp. 660-663. Word Count: 4022.
College Football pp. 654-656.
Petty, Richard (1937– ) pp. 139-140.
Starr, Bart (1934– ) pp. 697-698.
Gibson, Bob (1935– ) pp. 462-463.
Knight, Bobby (1940– ) pp. 190
Tarkanian, Jerry (1930– ) pp. 54.
Smith, Dean (1931– ) pp. 600
Shula, Don (1930– ) pp. 540-541.
Murray, Lenda (1962– ) pp. 668

The Scribner Encyclopedia of American Lives

The Scribner Encyclopedia of American Lives, Thematic Series: Sports Figures. Ed. Arnold Markoe and Kenneth T. Jackson. Vol. 1. New York: Charles Scribner's Sons, 2002. 392-394. Gale Virtual Reference Library. Web. 15 Jan. 2016.

Haskins, Donald Lee p. 392-394. Word Count: 1557. Eric Enders Vol. 1
Spahn, Warren Edward p. 380-382. Word Count: 1420. David Marc Vol. 2
Gaines, Clarence Edward, Sr. ("Bighouse") p. 312-314. Word Count: 1418. Lawson Bowling Vol. 1
Robinson, Edward Gay ("Eddie") p. 286-288. Word Count: 1286. J. Michael Butler Vol. 2
Petty, Richard Lee p. 240-242. Word Count: 1243. Kenneth Wayne Howell Vol. 2
Buchanan, Junious ("Buck") p. 128-130. Word Count: 1160. Michael Oriard Vol. 1
Longden, John Eric ("Johnny") p. 59-61. Word Count: 1126. Steven P. Savage Vol. 2

Dictionaries

United States

American Heritage Dictionary

win·ning·est (wĭnĭng-ĭst) adj. Informal. More successful or winning more often than any others of its kind: the winningest coach in college football.

Merriam Webster: "having achieved the most wins <the winningest coach in football>"

Oxford dictionaries

OED

winning , adj.

2. Gaining, or resulting in, victory or superiority in a contest or competition; victorious. In U.S. colloq. use also in superlative. winning hazard: see winning hazard at hazard n. 7b. winning stroke, a stroke that gains a point in a game, or one by which the game is won.

1599 Shakespeare Romeo & Juliet iii. ii. 12 Learne me how to loose a winning match.
1609 P. Holland tr. A. Marcellinus Rom. Hist. 290 Contemning that Emperour who everie where in civile warre went away on the winning hand.
1822 Scott Fortunes of Nigel I. Introd. Ep. p. xli, I am not displeased to find the game a winning one.
1855 Poultry Chron. 2 486 Neither should I have given the first place to the winning Dorking cock.
1860 Löwenthal Morphy's Games Chess 56 The winning move.
1884 Marshall's Tennis Cuts 114 In playing against a fine player, it is imperative to go for a winning-stroke whenever there is a fair opening.
1974 State (Columbia, S. Carolina) 5 Mar. 6- a/7 John Bates, coach of Maryland-Eastern Shore, at 26–1 the winningest college basketball team in the nation.
1979 Tucson (Arizona) Citizen 20 Sept. 5 d/1 Slota defeated Sarah Cap, the winningest active greyhound with 113 career victories.
1985 Dirt Bike Mar. 23/2 (advt.) That's the moment you know what the winningest racers and most satisfied riders know.

The New Zealand Oxford Dictionary Edited by Tony Deverson and Graeme Kennedy Publisher: Oxford University Press Print Publication Date: 2005 Print ISBN-13: 9780195584516 Published online: 2005

winningest /ˈwɪnɪŋəst/

▶ adjective esp. (US colloq.) having achieved the most success in competition.

Australian Oxford Dictionary (2 ed.)

Reference type: English Dictionary Current Version: 2004 Subject: English Dictionaries and Thesauri

winningest

... / ˈwɪnɪŋəst / ▶ adjective US colloq. having achieved the most success in competition ....

The Canadian Oxford Dictionary (2 ed.)

Reference type: English Dictionary Current Version: 2005 Subject English Dictionaries and Thesauri

winningest

... ▶ adjective N Amer. Sport informal that has won the most often; that has recorded or achieved the most victories ....

Oxford Dictionary of English (3 ed.)

Reference type: English Dictionary Current Version: 2015 Subject: English Dictionaries and Thesauri

winningest

... / 'wɪnɪŋɪst / ▶ adjective N. Amer. informal having achieved the most success in competition : the winningest coach in pro-football history . having achieved most success in competition winningest...

New Oxford American Dictionary (3 ed.)

Reference type: English Dictionary Current Version: 2015 Subject: English Dictionaries and Thesauri

winningest

... / 'winiNGist / ▶ adjective N. Amer. informal having achieved the most success in competition : the winningest coach in pro-football history . having achieved most success in competition winningest...

Other

Online Etymology Dictionary

winningest "Winningest is attested by 1804."
- Note This 1804 reference could be from the 1804 edition The False One, first published in 1647.[6].
- Appears in 1838 in Poems, Longer and Shorter By Thomas Burbidge
- Earliest Google Books reference using the winningest sports figure usage in US English is from 1948

Google Ngram Viewer

[7] comparison of winningest and most victorious

See also #Older uses below

Slang and related dictionaries that do NOT list winningest

The Oxford Dictionary of New Words. Elizabeth Knowles, Julia Elliott. Elizabeth Knowles, Julia Elliott. 2, reprint, revised. Oxford University Press, 1998. the University of California. 11-Dec-09. 0198602359, 9780198602354.
Slang: The Topical Dictionary of Americanisms. Paul Dickson. Bloomsbury Publishing USA, 2010. 0802718493, 9780802718495. 432 pages. Reference. › . Dictionaries.
The Oxford Dictionary of Slang. John Ayto. John Ayto. Oxford University Press, 1998. 019863157X, 9780198631576. 474 pages.
War Slang: American Fighting Words & Phrases Since the Civil War, Third Edition. Dover books on language. Paul Dickson. Courier Corporation, 2014. 0486797163, 9780486797168. 464 pages.
NTC's Dictionary of American Slang and Colloquial Expressions. Richard Spears. National Textbook Co. 1989 ISBN 0844254614
A Dictionary of Australian Colloquialisms. Gerald Alfred Wilkes. 2, illustrated, reprint. HarperCollins Publishers Australia, 1988. 0732224330, 9780732224332.
Dictionary of American Slang. Harold Wentworth, Stuart Berg Flexner. Harold Wentworth, Stuart Berg Flexner. 2. Crowell, 1975. 346849016X, 9783468490163.
American English: An Introduction. Zoltan Kovecses. Broadview Press, 2000. 1460403096, 9781460403099.
Cassell's Dictionary of Slang. Jonathon Green. revised. Sterling Publishing Company, Inc., 2005. 0304366366, 9780304366361.
Slang: The People's Poetry. Michael Adams. reprint. Oxford University Press, 2009. 0195314638, 9780195314632.
The Oxford Essential Dictionary of Word Histories. Glynnis Chantrell. Berkley Books, 2003. Pennsylvania State University. 29-Jun-09. 0425190986, 9780425190982.
The Concise New Partridge Dictionary of Slang and Unconventional English. Tom Dalzell, Terry Victor. Tom Dalzell, Terry Victor. revised. Routledge, 2014. 1317625129, 9781317625124.
The Columbia Guide to Standard American English. Kenneth George Wilson. Columbia University Press, 2013. 0585041482, 9780585041483.
The Bedford Guide for College Writers 6e With Reader, Research Manual, & Handbook C + Study Skills for College Writers. Kennedy, the Bedford Guide for College Writers, 4-In-1, Clot. Kennedy, Sidney, Dorothy M. Kennedy, X. J. Kennedy, Sylvia A. Holladay. 6. Macmillan Higher Education, 2001. 0312399510, 9780312399511. No mention of winningest in the troublesome words guide, or elsewhere

Newspapers

United States

The New York Times

The Wall Street Journal

The Washington Post

The Boston Globe

Chicago Tribune

Chicago Sun-Times

Air Force flies past Texas Chicago Sun-Times January 1, 1986; 550 words "...Falcons to a 24-16 victory over Texas in the 27th Bluebonnet Bowl in Houston's Rice Stadium. The Falcons closed their winningest season at 12-1. Texas finished at 8-4. Evans, who gained 129 yards on 18 carries, was named the game's most valuable...
Sting's Roberts stars on defense January 10, 1986; Lacy J. Banks; 632 words " ...ability because I am a natural forward. Few, if any, other defenders can say that." Coached by Don Popovic, the MISL's winningest coach ever, the Spirit, who played the Kansas City Comets last night, are paced offensively by forward Paul Child..."
Bo Ryan steps down as Wisconsin’s basketball coach December 16, 2015; 534 words " ...throwing his name in the hat for the full-time gig.In more than 14 seasons at the school, Ryan is 364–130. He’s the winningest coach in Wisconsin history and took the Badgers to the NCAA Tournament in each of his 14 seasons."

Los Angeles Times

The Philadelphia Inquirer

Dallas Morning News

Houston Chronicle

San Francisco Chronicle

The Detroit News

Seattle Times

Arizona Republic

USA Today

With Penn State wins restored, Joe Paterno the winningest coach again

Canadian newspapers

Toronto Star (largest Canadian newspaper)

The Globe and Mail (2nd largest Canadian newspaper)

Montreal Gazette

Older uses

Uses of the word in newspapers from the 19th and earlier 20th centuries include:

1862. Boston Post Wednesday, January 15, 1862, Boston, Massachusetts "…else she was not a Coquette. And then she is daintily made (A smile from the dainty Lizette) By people expert in the trade Of forming a proper Coquette. She has the winningest ways with the beaux, (Go on!—said the winning Lizette) But there isn’t a man of them knows The mind…"
1865. Farmer Bells' Thanksgiving. Centralia Sentinel. Thursday, December 21, 1865, Centralia, Illinois. "What cried the farmer, finding his voice at last. "Mine? Where'd you get it, Emily? You can't have wheeled old Grip out of a two thousand dollar mortgage for all you're the winningest bit of womankind alive. Mine Emily? Why this is the mortgage on my house!…"
1906. New York Times. Sunday, April 8, 1906, New York, New York. "Administration. - 4 Benjamin Harrison was a man of undoubted ability, with a singularly unfortunate personality. He,had what an old countryman of mine described as * the winningest way of making men hate him ’ of any man I ever knew. He so antagonized politicians in his own party that..."...
1920. Kansas City Times Saturday, July 17, 1920, Kansas City, Kansas. "Our Oil Boom Has Blown Up,” headlines the Rossviile Reporter sattly, but adds that Rossvilie may still derive a lot of satisfaction out of having one of the winningest hall teams in that part of the state. Jack Harrison of the Beloit Gazette see.s nothing remarkable in the case..."
1925. Centralia Evening Sentinel Friday, December 4, 1925, Centralia, Illinois. "...sister of Mrs. Shanks of Richview. ~ The next meeting will be beld v Cd Mrs. J. M. Haney, 219 East Kerr street; The Guudry children of Los Angeles are the prize-winningest children on record. Roland Charles, 4. and Lucjenne, 5, recently went through Europe and won every children..."

Based on a search of newspapers.com, the term appears to have begun to be used in its modern usage (i.e., having the most wins in a sporting context) in the 1920s or 1930s and to have become quite widespread by the late 1940s and 1950s. Such uses from earlier years include:

1930. Dubuque Telegraph Herald And Times Journal Monday, May 26, 1930, Dubuque, Iowa. "to strengthen his position as the major leagues’ winningest pitcher."
1932: "Roy Spencer ... will bet dough that Bump Hadley will be the winningest twirler in Chicago White Stockings this season"
1934: John McGraw - "Baseball's Winningest Pilot"
1936: road trip in which White Sox won 11 of 13 games was "the 'winningest' trip" for the club in years
1936: describing Vern Kennedy with 16 wins as the "Winningest Pitcher in the American League"
1937: describing Frank Thomas of Alabama as "America's winningest football coach"
1939: Winningest Family Has 637 Ribbons
1939: Dizzy Dean "is not only a winning pitcher, but just about the winningest pitcher there is"
1949: noting that the Salad Bowl featured the "winningest football team from Ohio" against the "winningest team in Arizona"
1949: referring to Frank Leahy as "the winningest football coach in America"
1949: describing Ann Olson, winner of 12 national championships, as "the winningest diver the United States has ever produced"
1949: "America's winningest jockey, Johnny Longden, climaxed his winningest year ..."
1949: with 15 victories in mid July, Vic Raschi was "the winningest pitcher in the majors"
1950: describing Frank Leahy and Bud Wilkinson as "the two winningest coaches in modern American football"

Wire services

Associated Press

Reuters

UPI

Magazines

United States

Time

Newsweek

Sports Illustrated

Other

The Economist

The woman's touch. (jockey Julie Krone) August 14, 1993; 700+ words "...vacation's riding on you, Krone." Does Ms Krone deserve these threats? She is, as Americans put it, one of the most winningest jockeys. In June she became the first woman, anywhere in the world, to win a classic race, when in splendidly driving..."

Broadcast networks

BBC

16 November, 2000. Hull sheaths Sabres once more. "Roy, the NHL's winningest goalie, made 41 saves to become the 19th player with 50 shutouts."
25 October, 2003. McRae: End of the road? "Four years at Ford earned him enough victories to make the him what Americans would call the winningest rally driver of all time."
3 January, 2005. College bowls round-up. "In the Outback Bowl in Tampa, David Greene, the winningest quarterback in NCAA history, enjoyed one last victory as Georgia beat Wisconsin 24-21. "
15 September 2008. Matt Roberts' MotoGP round-up. Matt Roberts. BBC Sport at Indianapolis. "And it allowed Valentino Rossi - as they would say over here, the all-time winningest rider in the sport's history - to make further history as the first MotoGP winner at Indy, in what turned out to be an otherwise damp squib of a weekend."
3 January 2012. Sportsday Live. "0950 AMERICAN FOOTBALL: Penn State's Joe Paterno, the 'winningest' coach in major college football history who was fired in November over a child sexual abuse scandal, died on Sunday of lung cancer. "
11 August 2012. London 2012 Diary: Offbeat snippets from around the Games - day 15. "Mike Krzyzewski became 'Division I’s winningest coach' in November 2011 "
11 May 2014. Eurovision 2014: Reporter's diary. Sarah Jane Griffiths Entertainment and Arts reporter, BBC News, Copenhagen. "'It just gets better for Molly!' he said this morning. 'The last song has won Eurovision six times. It's the 2nd most 'winningest' spot in the draw after 17th.' "

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