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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Hugo Brederode | 41 | 1963-1968 | |
| 1 | Steve Ferguson# | 41 | 1973-1978 | |
| 3 | Andy Flowers* | 38 | 1955-1959 | |
| 4 | Pat Egglestone | 37 | 1935-1938 | |
| 5 | Alejandro Sánchez | 35 | 1936-1939 | |
| 5 | William Wilson# | 35 | 1979-1983 | |
| 7 | Davis Ayliffe# | 29 | 1978-1981 | |
| 7 | José Molina | 29 | 1962-1967 | |
| 7 | Claudio Romero# | 29 | 1976-1980 | |
| 7 | Clancy Swanson | 29 | 1944-1948 | |
| 11 | Bill Hansen | 28 | 1913-1916 | |
| 12 | Jeff Brown | 27 | 1955-1959 | |
| 13 | Nicholas Cassidy | 26 | 1969-1972 | |
| 13 | Ryan Duncan | 26 | 1941-1944 | |
| 13 | Jim Morton* | 26 | 1961-1964 | |
| 13 | Orlando Ramírez | 26 | 1977-1981 | |
| 13 | Steve Sommer | 26 | 1936-1938 | |
| 18 | Travis Brown | 25 | 1961-1964 | |
| 18 | Rod Johnston | 25 | 1958-1961 | |
| 18 | Anthony Moore | 25 | 1961-1964 | |
| 18 | Luis Ortega | 25 | 1953-1956 | |
| 18 | Gustavo Salas | 25 | 1927-1930 | |
| 18 | Cris Vilardebo# | 25 | 1982-1986 | |
| 24 | Jimmy Bacon# | 24 | 1972-1974 | |
| 24 | Eric Carlisle | 24 | 1927-1930 | |
| 24 | Domingo Fajardo | 24 | 1927-1930 | |
| 24 | José García | 24 | 1953-1956 | |
| 24 | Ron Griffin | 24 | 1926-1929 | |
| 24 | Norm Harris# | 24 | 1983-1986 | |
| 24 | Sancho Hernández# | 24 | 1983-1986 | |
| 24 | Armando Rivera | 24 | 1919-1922 | |
| 24 | Freddy Rosado | 24 | 1957-1960 | |
| 33 | Kel Brooks* | 23 | 1927-1930 | |
| 33 | Ricardo Rico# | 23 | 1970-1973 | |
| 33 | Francisco Rivera | 23 | 1971-1974 | |
| 33 | Ambrose Sanders# | 23 | 1977-1980 | |
| 33 | Brock Tebby | 23 | 1937-1940 | |
| 33 | Teddy Turner | 23 | 1974-1977 | |
| 39 | José Álvarez | 22 | 1961-1966 | |
| 39 | Manuel Castaneda | 22 | 1948-1951 | |
| 39 | Rob Davis# | 22 | 1976-1979 | |
| 39 | Tom Hayes | 22 | 1935-1938 | |
| 39 | Allen Haynes | 22 | 1974-1977 | |
| 39 | Jim Lyons | 22 | 1963-1966 | |
| 39 | Freddy Pérez | 22 | 1958-1961 | |
| 39 | Jason Sanders | 22 | 1952-1955 | |
| 39 | Paul Williams | 22 | 1911-1915 | |
| 48 | Peter Alexander# | 21 | 1982-1985 | |
| 48 | Keith Hayes | 21 | 1931-1935 | |
| 48 | Raúl Jiménez | 21 | 1962-1966 | |
| 48 | Ignacio Palácios | 21 | 1954-1957 | |
| 48 | Robert Reese | 21 | 1911-1914 | |
| 53 | Randy Bailey | 20 | 1917-1921 | |
| 53 | Ricardo Barrera# | 20 | 1985-1988 | |
| 53 | William Lee# | 20 | 1983-1986 | |
| 53 | Lorenzo Maldonado | 20 | 1973-1976 | |
| 53 | Curtis Orr | 20 | 1911-1915 | |
| 53 | Armando Rea | 20 | 1926-1929 | |
| 53 | Patrick Smith | 20 | 1930-1932 | |
| 53 | Bill Warren | 20 | 1929-1932 | |
| 61 | Herb Bird | 19 | 1913-1916 | |
| 61 | Woodrow Davis* | 19 | 1954-1957 | |
| 61 | Eduardo Delpino# | 19 | 1976-1980 | |
| 61 | Jon Ellis | 19 | 1942-1943 | |
| 61 | Bob Johnston | 19 | 1920-1922 | |
| 61 | Cam Knap | 19 | 1967-1971 | |
| 61 | Ángel Lombos | 19 | 1918-1921 | |
| 61 | Pat Miller | 19 | 1957-1960 | |
| 61 | Chris Reynolds* | 19 | 1911-1914 | |
| 61 | Sergio Vásquez | 19 | 1966-1969 | |
| 61 | Danny Ventura# | 19 | 1987-1990 | |
| 61 | Richard Ward* | 19 | 1919-1922 | |
| 61 | Yong-koo Yi# | 19 | 1985-1988 | |
| 74 | Guy Boyd# | 18 | 1978-1982 | |
| 74 | Pedro Correa | 18 | 1921-1923 | |
| 74 | Marty Hensley* | 18 | 1952-1955 | |
| 74 | Duncan Johnson# | 18 | 1988-1991 | |
| 74 | Gustavo Marroquín | 18 | 1911-1914 | |
| 74 | Ellis Masters | 18 | 1917-1920 | |
| 74 | Júlio Mayen# | 18 | 1987-1988 | |
| 74 | Mal Wright | 18 | 1916-1919 | |
| 82 | Leroy Beatty | 17 | 1952-1955 | |
| 82 | Homer Carter | 17 | 1916-1920 | |
| 82 | Mortimer Cold | 17 | 1917-1920 | |
| 82 | Zi-yang Cuan | 17 | 1941-1944 | |
| 82 | Félix Díaz | 17 | 1966-1969 | |
| 82 | Johnny Downey | 17 | 1967-1970 | |
| 82 | Alfredo Enríquez# | 17 | 1983-1986 | |
| 82 | Ricardo Flores | 17 | 1956-1959 | |
| 82 | António González | 17 | 1917-1920 | |
| 82 | José González | 17 | 1911-1914 | |
| 82 | Jay Gregg | 17 | 1911-1916 | |
| 82 | Naomichi Ine | 17 | 1964-1965 | |
| 82 | Shawn Johnson | 17 | 1929-1932 | |
| 82 | Johnny Jones | 17 | 1921-1923 | |
| 82 | Steffen Lewis | 17 | 1934-1936 | |
| 82 | Luis Martínez | 17 | 1968-1972 | |
| 82 | Elliott Mathews | 17 | 1965-1968 | |
| 82 | Gustavo Miranda# | 17 | 1975-1978 | |
| 82 | Gilbert Mitchell# | 17 | 1984-1986 |
