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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Esteban Martínez | 125 | 2017-2029 | |
| 2 | Michael Walsh | 118 | 2025-2039 | |
| 3 | Yeong-suk Kim | 106 | 2021-2034 | |
| 4 | Alberto Rivera | 101 | 2022-2035 | |
| 5 | Marcus Seraphin# | 99 | 2048-2056 | |
| 6 | Luis Rodríguez | 98 | 2033-2043 | |
| 7 | Joe Kenner | 94 | 2019-2033 | |
| 8 | Joey Cabler | 90 | 2043-2050 | |
| 9 | Jeffery Francis | 89 | 2016-2027 | |
| 9 | Bernardo Lara | 89 | 2016-2029 | |
| 11 | Ashley Heath | 87 | 2028-2040 | |
| 11 | Dennis Montgomery | 87 | 2030-2042 | |
| 13 | John Martin | 86 | 2012-2021 | |
| 14 | Edgar Alvarez | 85 | 2036-2047 | |
| 14 | Ken Stein | 85 | 2034-2045 | |
| 14 | Daniel Wilson | 85 | 2023-2033 | |
| 17 | Jeff Bushman | 84 | 2040-2049 | |
| 17 | Robert Cook | 84 | 2021-2036 | |
| 17 | Goro Ota | 84 | 2029-2039 | |
| 20 | Eddie Beltran | 83 | 2042-2054 | |
| 20 | Dongdo-pa Chen | 83 | 2025-2039 | |
| 20 | Edgardo Félix | 83 | 2015-2029 | |
| 20 | Trey Robinson | 83 | 2024-2035 | |
| 24 | Kagehisa Saikawa | 82 | 2022-2035 | |
| 24 | Jacob Willard | 82 | 2024-2038 | |
| 26 | Josh Bradshaw | 81 | 2039-2049 | |
| 27 | Douggie Pitchford | 80 | 2030-2042 | |
| 27 | Chris Sanchez | 80 | 2035-2047 | |
| 27 | Masamichi Takeda | 80 | 2031-2040 | |
| 30 | Chuk-yan Bi | 78 | 2022-2033 | |
| 31 | Alain Picard | 77 | 2030-2042 | |
| 32 | Wayne Penfield | 76 | 2020-2029 | |
| 33 | Leonard Lee | 75 | 2026-2034 | |
| 33 | Carlos León | 75 | 2022-2033 | |
| 33 | Ichiji Seaton# | 75 | 2048-2057 | |
| 36 | Alex Munoz | 74 | 2034-2044 | |
| 36 | Michael Smith | 74 | 2027-2037 | |
| 38 | Joel Hyle# | 73 | 2052-2057 | |
| 38 | Jason Shaw# | 73 | 2048-2056 | |
| 38 | Danny Zomosa | 73 | 2035-2044 | |
| 41 | Héctor Bello | 72 | 2034-2044 | |
| 41 | Ron Harris | 72 | 2035-2045 | |
| 43 | Andrew Johnson | 71 | 2028-2037 | |
| 43 | Anthony McIntyre | 71 | 2022-2034 | |
| 45 | Andres Alvarez# | 70 | 2043-2057 | |
| 45 | Mike Brown | 70 | 2046-2056 | |
| 45 | Joe Gillard | 70 | 2031-2038 | |
| 45 | Jon Morris | 70 | 2019-2028 | |
| 45 | Jun Nakayama | 70 | 2026-2041 | |
| 50 | Peter Barrett | 69 | 2012-2021 | |
| 50 | Rick Childress | 69 | 2026-2034 | |
| 50 | Robert Hood | 69 | 2015-2023 | |
| 53 | Po-sin Pang | 68 | 2029-2040 | |
| 53 | Pat Toope# | 68 | 2051-2057 | |
| 55 | Pedro Aragon | 67 | 2048-2055 | |
| 55 | Bob Campos | 67 | 2035-2047 | |
| 55 | Jeremy Lamfers# | 67 | 2047-2057 | |
| 58 | Dan Ayers | 66 | 2043-2050 | |
| 58 | Pablo Cuevas | 66 | 2015-2029 | |
| 58 | Felix Martinez | 66 | 2042-2050 | |
| 61 | Jim Ashford# | 65 | 2049-2057 | |
| 61 | Pedro Cerna | 65 | 2033-2048 | |
| 61 | Pablo Costa | 65 | 2015-2028 | |
| 61 | Scott Gorman | 65 | 2012-2022 | |
| 61 | Nelson Hill | 65 | 2014-2025 | |
| 61 | Gene Legrow | 65 | 2043-2052 | |
| 61 | Jason Reeves | 65 | 2045-2052 | |
| 61 | Scott Siket# | 65 | 2048-2054 | |
| 69 | Leland Bullins | 64 | 2033-2041 | |
| 69 | Teagan Cooper | 64 | 2038-2047 | |
| 69 | Chris Costello | 64 | 2037-2045 | |
| 69 | Harold Hayne | 64 | 2023-2035 | |
| 69 | Yoshiyuki Matsuda | 64 | 2038-2045 | |
| 74 | Carlos Carballo | 63 | 2037-2048 | |
| 74 | Gerardo Estrada | 63 | 2023-2034 | |
| 74 | Robby Martin# | 63 | 2048-2055 | |
| 74 | J.R. Murphy | 63 | 2016-2025 | |
| 74 | Alex Rivas | 63 | 2035-2042 | |
| 74 | Devayukta Tushar | 63 | 2023-2032 | |
| 80 | Steve Johnston | 62 | 2016-2023 | |
| 80 | Bappaka Ramanakoppa | 62 | 2022-2038 | |
| 80 | Miguel Rodríguez | 62 | 2034-2045 | |
| 80 | Omar Salazar# | 62 | 2047-2057 | |
| 84 | Shawn Carl# | 61 | 2048-2057 | |
| 84 | Kazuhiro Kouno | 61 | 2020-2027 | |
| 84 | Michael Moyer | 61 | 2022-2037 | |
| 87 | Tommy Bartlett | 60 | 2021-2029 | |
| 87 | Juan Centeno | 60 | 2038-2047 | |
| 87 | Ramón Gómez | 60 | 2027-2039 | |
| 87 | John Huo | 60 | 2033-2042 | |
| 87 | Jay McCarter | 60 | 2040-2047 | |
| 87 | Su-gyung Park | 60 | 2029-2040 | |
| 87 | Scott Roberts | 60 | 2019-2029 | |
| 87 | Ernesto Sanchez# | 60 | 2047-2057 | |
| 95 | Chris Baxter | 59 | 2019-2026 | |
| 95 | Arturo González | 59 | 2013-2028 | |
| 95 | John Holmes | 59 | 2025-2029 | |
| 95 | Joe McLernon | 59 | 2016-2022 | |
| 95 | David Myers | 59 | 2029-2039 | |
| 95 | Pat Nettles# | 59 | 2052-2057 |
