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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Henry Valentine | 116 | 2021-2031 | |
| 2 | Clive Smedley | 111 | 2026-2039 | |
| 3 | Elvis Warren | 108 | 2030-2041 | |
| 4 | Luis Pérez | 104 | 2021-2033 | |
| 5 | Mark Clark | 100 | 2030-2048 | |
| 6 | Grant Clark | 86 | 2029-2043 | |
| 7 | Carlos Montaño | 83 | 2040-2049 | |
| 8 | David Franklin | 80 | 2033-2041 | |
| 9 | Adam Berry | 79 | 2015-2025 | |
| 9 | Ed Harris | 79 | 2018-2022 | |
| 9 | Bobby Sanders | 79 | 2028-2042 | |
| 12 | Ángel Cisneros | 78 | 2025-2035 | |
| 13 | Jud Bradford# | 77 | 2039-2051 | |
| 14 | Mario Contreras# | 73 | 2038-2051 | |
| 15 | Eric Lewis | 72 | 2040-2050 | |
| 16 | Tim Davis | 71 | 2016-2023 | |
| 17 | Clint Smith | 70 | 2028-2037 | |
| 18 | Robert Collard | 69 | 2030-2046 | |
| 18 | José Pacheco | 69 | 2029-2040 | |
| 18 | Shih-k'ai Su-Tu | 69 | 2036-2047 | |
| 21 | Rod Duncan | 68 | 2043-2050 | |
| 21 | Jorge Mendoza | 68 | 2038-2044 | |
| 21 | Wynn Thompson | 68 | 2020-2036 | |
| 24 | Bryan Bradshaw | 67 | 2031-2043 | |
| 24 | Héctor Rodríguez | 67 | 2026-2034 | |
| 26 | Bill Blair | 66 | 2025-2035 | |
| 26 | Olivier Martel | 66 | 2031-2042 | |
| 28 | Willis Hines | 65 | 2029-2037 | |
| 29 | Stan Long | 63 | 2025-2030 | |
| 30 | Dave Lynch | 62 | 2035-2046 | |
| 30 | Dan MacGruder | 62 | 2021-2026 | |
| 32 | Dan Gibson# | 61 | 2043-2051 | |
| 32 | Stu Miller | 61 | 2029-2038 | |
| 32 | Michael Taylor | 61 | 2037-2046 | |
| 32 | David White | 61 | 2031-2037 | |
| 36 | Patrick Davis | 60 | 2030-2041 | |
| 37 | Juan Bonilla | 59 | 2031-2042 | |
| 37 | Kelly Cooper | 59 | 2033-2041 | |
| 37 | Joe McCabe | 59 | 2033-2041 | |
| 40 | Bill Wall | 58 | 2032-2041 | |
| 41 | Joe Hunt | 57 | 2026-2034 | |
| 41 | Steve Lewis | 57 | 2025-2032 | |
| 43 | Clark Crawford | 56 | 2030-2038 | |
| 43 | Barrett Dobson | 56 | 2034-2041 | |
| 43 | Arnaldo Magaldi | 56 | 2011-2017 | |
| 43 | Dave Michael | 56 | 2030-2041 | |
| 43 | Octávio Morales# | 56 | 2045-2051 | |
| 48 | Santiago Alonso | 55 | 2010-2015 | |
| 48 | Randolph Hutchison | 55 | 2020-2029 | |
| 48 | Juan Martínez | 55 | 2026-2033 | |
| 48 | Raúl Medine | 55 | 2025-2037 | |
| 48 | David Rivera | 55 | 2025-2031 | |
| 48 | Wilbert Sutton | 55 | 2034-2040 | |
| 48 | Ricardo Tobías | 55 | 2014-2018 | |
| 55 | Phil Jackson | 54 | 2027-2040 | |
| 55 | Matt Roberts | 54 | 2021-2036 | |
| 55 | Paul Ross | 54 | 2029-2040 | |
| 55 | Raymundo Vogado | 54 | 2038-2049 | |
| 59 | William Brown | 53 | 2033-2038 | |
| 59 | Edward Lee | 53 | 2021-2034 | |
| 59 | Raúl Morán | 53 | 2039-2050 | |
| 59 | César Román | 53 | 2038-2043 | |
| 63 | Jeff Childress | 52 | 2039-2049 | |
| 63 | Isoruko Hayagawa# | 52 | 2044-2051 | |
| 63 | Félix Mendoza | 52 | 2039-2049 | |
| 63 | Franklin Price | 52 | 2036-2043 | |
| 63 | Brady Walker | 52 | 2038-2045 | |
| 63 | Takashi Yokoyama# | 52 | 2046-2051 | |
| 69 | Jim Daly | 51 | 2039-2046 | |
| 69 | Jud Horn | 51 | 2024-2036 | |
| 69 | Harry McCain | 51 | 2040-2048 | |
| 72 | Michael Cater | 50 | 2042-2050 | |
| 72 | Jorge Gómez | 50 | 2034-2043 | |
| 72 | Bill Morales | 50 | 2032-2037 | |
| 72 | Eric Tanner | 50 | 2016-2023 | |
| 76 | Bob Collins | 49 | 2018-2024 | |
| 76 | Tony García | 49 | 2036-2045 | |
| 76 | Ánibal Guzmán | 49 | 2025-2030 | |
| 76 | Gregg McClendon | 49 | 2016-2024 | |
| 76 | Howard Parker# | 49 | 2044-2051 | |
| 81 | Chris Cochrane# | 48 | 2042-2051 | |
| 81 | Ernesto Garza | 48 | 2044-2049 | |
| 81 | Thatcher Norman | 48 | 2030-2039 | |
| 81 | Leonard Ralston | 48 | 2032-2047 | |
| 81 | Luis Tapia | 48 | 2027-2033 | |
| 81 | Miles van Veen | 48 | 2037-2044 | |
| 81 | Victor Vinson | 48 | 2021-2029 | |
| 81 | Dale Warren | 48 | 2021-2031 | |
| 89 | Lee Clark | 47 | 2034-2037 | |
| 89 | Ángel García | 47 | 2025-2034 | |
| 89 | Hunter Richardson | 47 | 2024-2031 | |
| 89 | Gavin Sarkies | 47 | 2033-2039 | |
| 89 | Mitsuhide Suzuki | 47 | 2034-2046 | |
| 94 | Darby Clark | 46 | 2021-2025 | |
| 94 | Troy MacNider | 46 | 2022-2029 | |
| 94 | Clint Potts | 46 | 2028-2044 | |
| 94 | Mauro Puñal | 46 | 2012-2019 | |
| 94 | Craig Robinson | 46 | 2043-2047 | |
| 99 | John Murphy | 45 | 2033-2046 | |
| 99 | Arturo Valadez | 45 | 2035-2042 |
