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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Steve Flowers# | 84 | 2053-2062 | |
| 2 | Ed Byrnes | 79 | 2034-2041 | |
| 3 | Jorge Valarcel | 73 | 2037-2047 | |
| 4 | Ed Fisher | 68 | 2023-2030 | |
| 4 | Rubén Herrera | 68 | 2048-2055 | |
| 4 | Zenon-Alejandro Paez | 68 | 2034-2045 | |
| 7 | José García | 67 | 2029-2036 | |
| 8 | Mike Cox | 66 | 2042-2047 | |
| 9 | Leon Misner | 65 | 2034-2041 | |
| 10 | Eric Turner | 62 | 2028-2037 | |
| 10 | Albert Valverde | 62 | 2048-2058 | |
| 12 | Sam King | 61 | 2013-2023 | |
| 12 | Marçall Rivera | 61 | 2025-2033 | |
| 14 | Xavier Colón | 60 | 2036-2044 | |
| 15 | Jim Frost# | 59 | 2053-2062 | |
| 16 | Bobby Higgins | 58 | 2034-2043 | |
| 16 | António Maldonado | 58 | 2043-2053 | |
| 16 | Reginald McDaniel | 58 | 2039-2048 | |
| 16 | Steve Miller | 58 | 2037-2044 | |
| 20 | Julián Correa | 57 | 2030-2037 | |
| 20 | Eli García | 57 | 2024-2032 | |
| 20 | José Tobías | 57 | 2022-2026 | |
| 23 | Jesús Montoya | 55 | 2038-2045 | |
| 23 | Alfredo Pérez | 55 | 2047-2055 | |
| 23 | Jim Sheehan | 55 | 2050-2058 | |
| 26 | Xavier Quinn | 54 | 2037-2044 | |
| 27 | Hang-fu Che# | 53 | 2055-2064 | |
| 27 | Heui-chung Chon# | 53 | 2055-2062 | |
| 27 | Don Wood | 53 | 2024-2031 | |
| 30 | Bob Beenhakker | 52 | 2032-2041 | |
| 30 | Arturo Castro# | 52 | 2053-2062 | |
| 30 | Devin Spicer | 52 | 2018-2025 | |
| 30 | Jorge Torrez | 52 | 2034-2040 | |
| 34 | Derek Boyd | 51 | 2020-2028 | |
| 34 | Clarence Collins# | 51 | 2054-2063 | |
| 34 | Tim Marshall | 51 | 2017-2025 | |
| 34 | Meiji Ohayashi | 51 | 2043-2046 | |
| 34 | Teizo Suzuki# | 51 | 2055-2063 | |
| 39 | Brodie Skuse | 50 | 2039-2046 | |
| 40 | Jim Upchurch# | 49 | 2059-2064 | |
| 41 | Max Blue | 48 | 2049-2053 | |
| 41 | Mike Cheney# | 48 | 2058-2064 | |
| 41 | Dan Cunningham | 48 | 2042-2048 | |
| 41 | Ernesto Guzalán | 48 | 2038-2042 | |
| 41 | Ed Haney | 48 | 2014-2024 | |
| 41 | José Madrid | 48 | 2021-2024 | |
| 41 | Pancho Martínez# | 48 | 2051-2059 | |
| 41 | Earl Moriarty# | 48 | 2056-2064 | |
| 41 | Donnie Skinner | 48 | 2021-2025 | |
| 50 | Phil Brooks | 47 | 2016-2024 | |
| 50 | Artie Church | 47 | 2018-2028 | |
| 52 | Jorge Cervantes | 46 | 2025-2036 | |
| 52 | Rodrigo López# | 46 | 2057-2063 | |
| 52 | Shizuka Sato# | 46 | 2057-2064 | |
| 52 | Efrain Sorebillo# | 46 | 2061-2064 | |
| 56 | José López# | 45 | 2052-2061 | |
| 56 | Rodrigo Morales | 45 | 2039-2043 | |
| 56 | Joaquín Rodríguez | 45 | 2037-2040 | |
| 56 | Bob Stokes | 45 | 2016-2020 | |
| 60 | Kevin Casey | 44 | 2034-2039 | |
| 61 | Victor Arango# | 43 | 2057-2064 | |
| 61 | Jim Burks | 43 | 2040-2048 | |
| 61 | Bubba Johnson | 43 | 2035-2045 | |
| 61 | Daniel León | 43 | 2034-2044 | |
| 61 | Mike Martin# | 43 | 2060-2064 | |
| 61 | Raúl Pérez | 43 | 2041-2047 | |
| 61 | Yun-qi Ying# | 43 | 2055-2064 | |
| 68 | Jesús Fernández | 42 | 2025-2029 | |
| 68 | Luis Galló | 42 | 2034-2040 | |
| 68 | Dan García | 42 | 2048-2052 | |
| 68 | Bob Gilbert | 42 | 2032-2040 | |
| 68 | Ken Lewis | 42 | 2013-2025 | |
| 68 | Mike Madison | 42 | 2051-2059 | |
| 68 | Harry Morgan# | 42 | 2050-2059 | |
| 68 | Steve O'Keefe | 42 | 2034-2044 | |
| 68 | Jim Wilson | 42 | 2038-2045 | |
| 77 | Víctor García | 41 | 2035-2040 | |
| 77 | Bo Grant# | 41 | 2056-2061 | |
| 77 | Randy Maire# | 41 | 2057-2063 | |
| 77 | Shoin Mori | 41 | 2024-2028 | |
| 77 | Bob Peterson | 41 | 2024-2033 | |
| 77 | Greg Snyder# | 41 | 2053-2056 | |
| 77 | José Valdés | 41 | 2042-2045 | |
| 84 | Rubén Aguilera | 40 | 2035-2040 | |
| 84 | Jake Howard | 40 | 2016-2019 | |
| 84 | Chuck Jenkins | 40 | 2013-2022 | |
| 84 | Iván León | 40 | 2028-2030 | |
| 84 | Sakutaro Nakano# | 40 | 2053-2058 | |
| 84 | Ken Nelson | 40 | 2013-2023 | |
| 90 | Jesús Bermúdez | 39 | 2045-2049 | |
| 90 | Stan Harrell | 39 | 2032-2040 | |
| 90 | Curt Keller | 39 | 2035-2040 | |
| 90 | Nick McGuire# | 39 | 2059-2064 | |
| 90 | Freddy Pueblo | 39 | 2018-2025 | |
| 90 | Dominic Siddell | 39 | 2053-2060 | |
| 96 | Yannick Clément# | 38 | 2056-2064 | |
| 96 | Tyler Doyle# | 38 | 2054-2062 | |
| 96 | Virgil Lee# | 38 | 2056-2064 | |
| 96 | Alfredo Montaño | 38 | 2023-2030 | |
| 96 | Dave Robles# | 38 | 2056-2064 |
