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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ronnie Wilson | 23 | 2038-2041 | |
| 2 | Robbie Daniel | 22 | 2015-2018 | |
| 2 | Bill Riggs# | 22 | 2036-2039 | |
| 4 | Howard Duque# | 21 | 2042-2045 | |
| 4 | Steve Elliott# | 21 | 2045-2048 | |
| 4 | Tom Green# | 21 | 2041-2044 | |
| 4 | Barton Johnson | 21 | 2016-2019 | |
| 4 | Héctor Ángel# | 21 | 2045-2048 | |
| 9 | Eric Fournet# | 20 | 2044-2047 | |
| 9 | Carlos Gutiérrez# | 20 | 2036-2039 | |
| 9 | Pat Key# | 20 | 2036-2039 | |
| 9 | John King# | 20 | 2045-2048 | |
| 13 | Steven Brooks | 19 | 2036-2039 | |
| 13 | Júlio Cabrera# | 19 | 2046-2049 | |
| 13 | Carl Morgan# | 19 | 2038-2041 | |
| 13 | Ramón Quintero | 19 | 2014-2017 | |
| 17 | Sean Aleksic# | 18 | 2042-2045 | |
| 17 | Leonard Ames# | 18 | 2040-2043 | |
| 17 | Bill Bryant# | 18 | 2046-2049 | |
| 17 | Sergio Encarnación# | 18 | 2046-2049 | |
| 17 | Clarence Fisher# | 18 | 2038-2041 | |
| 17 | Juan Franco | 18 | 2014-2017 | |
| 17 | Ricardo Guichardo | 18 | 2017-2020 | |
| 17 | Brian Hull | 18 | 2017-2020 | |
| 17 | Alco Krook# | 18 | 2045-2048 | |
| 17 | Jeff Lynn | 18 | 2017-2020 | |
| 17 | Troy Lynn | 18 | 2014-2017 | |
| 17 | Michihiro Naito# | 18 | 2046-2049 | |
| 29 | Mark Barton# | 17 | 2042-2045 | |
| 29 | Ron Cobb# | 17 | 2041-2044 | |
| 29 | Brendon Cummings# | 17 | 2044-2047 | |
| 29 | Dave Ford# | 17 | 2046-2049 | |
| 29 | Tracy Graham# | 17 | 2036-2039 | |
| 29 | Paul Gulley# | 17 | 2037-2040 | |
| 29 | Dave Lee# | 17 | 2039-2042 | |
| 29 | Dave Little# | 17 | 2037-2040 | |
| 29 | Hubert Nicol# | 17 | 2038-2041 | |
| 29 | Aaron Palmer | 17 | 2016-2019 | |
| 29 | Johnathan Phillips | 17 | 2015-2018 | |
| 29 | John Pitts | 17 | 2036-2039 | |
| 29 | Júlio Rodríguez# | 17 | 2040-2043 | |
| 29 | Christopher Smith# | 17 | 2040-2043 | |
| 29 | Samuel Wesman# | 17 | 2043-2045 | |
| 29 | Joe Wither# | 17 | 2046-2049 | |
| 45 | Tom Beaty | 16 | 2037-2040 | |
| 45 | Dwight Camp# | 16 | 2041-2044 | |
| 45 | Herman Carey# | 16 | 2046-2049 | |
| 45 | Brett Coker# | 16 | 2046-2049 | |
| 45 | Mark Collins* | 16 | 2014-2017 | |
| 45 | Mike Crawford# | 16 | 2042-2045 | |
| 45 | Juan Cruz# | 16 | 2042-2045 | |
| 45 | Mike Gibson# | 16 | 2042-2045 | |
| 45 | Manuel Gil | 16 | 2019-2021 | |
| 45 | Stanley Inman | 16 | 2013-2016 | |
| 45 | Robbie Kenney# | 16 | 2046-2049 | |
| 45 | Doug Lee# | 16 | 2036-2039 | |
| 45 | George Milley# | 16 | 2046-2049 | |
| 45 | Felipe Montés# | 16 | 2036-2039 | |
| 45 | David Morán# | 16 | 2045-2048 | |
| 45 | Chad O'Slattery# | 16 | 2040-2043 | |
| 45 | Jim Perry# | 16 | 2045-2048 | |
| 62 | Darren Blackwell | 15 | 2018-2021 | |
| 62 | Miguel Díaz | 15 | 2014-2017 | |
| 62 | Steve Edwards# | 15 | 2045-2048 | |
| 62 | Barry Garner | 15 | 2019-2022 | |
| 62 | Pat Gibbs# | 15 | 2042-2045 | |
| 62 | Butch Henderson# | 15 | 2040-2043 | |
| 62 | Ezra Mannington# | 15 | 2046-2049 | |
| 62 | Alejandro Méndez | 15 | 2013-2015 | |
| 62 | Merlin Peterson# | 15 | 2041-2044 | |
| 62 | Donald Richard# | 15 | 2046-2049 | |
| 62 | Everett Riley# | 15 | 2046-2049 | |
| 62 | Dan Rogers | 15 | 2015-2018 | |
| 62 | Maurice Towse | 15 | 2020-2022 | |
| 62 | Morris Wagner# | 15 | 2045-2048 | |
| 62 | John Ward# | 15 | 2038-2041 | |
| 62 | Rick Wortham# | 15 | 2046-2049 | |
| 78 | Fernando Acevedo# | 14 | 2040-2043 | |
| 78 | Markus Blackwell# | 14 | 2036-2039 | |
| 78 | Pete Brooks# | 14 | 2041-2044 | |
| 78 | Bart Brown | 14 | 2022-2025 | |
| 78 | Michael Brown# | 14 | 2042-2045 | |
| 78 | Wesley Burrows# | 14 | 2045-2048 | |
| 78 | Andrew Chambers# | 14 | 2043-2045 | |
| 78 | Will Clark# | 14 | 2045-2048 | |
| 78 | Larry Green# | 14 | 2046-2049 | |
| 78 | Edgardo Guzmán | 14 | 2014-2017 | |
| 78 | Jim Hicks | 14 | 2014-2017 | |
| 78 | Matt Hoffman# | 14 | 2043-2045 | |
| 78 | Joe Johnston# | 14 | 2036-2039 | |
| 78 | Pat Lockyer# | 14 | 2047-2049 | |
| 78 | Bob Magee# | 14 | 2044-2047 | |
| 78 | Mike Martin# | 14 | 2045-2048 | |
| 78 | Vaughan Martin# | 14 | 2039-2042 | |
| 78 | Colin Mason# | 14 | 2039-2042 | |
| 78 | Marc McIntyre# | 14 | 2043-2046 | |
| 78 | José Quintero# | 14 | 2046-2049 | |
| 78 | Domingo Rodríguez# | 14 | 2046-2049 | |
| 78 | Nicholas Ryding# | 14 | 2046-2049 | |
| 78 | Sam Simmons# | 14 | 2036-2039 |
