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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Andres Ochoa# | 65 | 2089-2094 | |
| 2 | Luis Gandara# | 50 | 2086-2090 | |
| 3 | Shigeru Nagamine# | 49 | 2094-2097 | |
| 4 | Micah Morgan# | 48 | 2092-2096 | |
| 5 | Roger Auvil | 45 | 2067-2075 | |
| 6 | Sam Schlangen | 40 | 2090-2092 | |
| 7 | Scott May# | 38 | 2091-2095 | |
| 7 | Dean Thomas# | 38 | 2092-2097 | |
| 9 | Mike Rumschlag# | 37 | 2091-2093 | |
| 10 | Zach Gaston# | 36 | 2094-2098 | |
| 10 | Oscar Mejia | 36 | 2071-2073 | |
| 12 | Josh Pecoraro | 35 | 2076-2078 | |
| 13 | Josh Brockway | 34 | 2074-2075 | |
| 13 | Jerry Jones | 34 | 2072-2077 | |
| 13 | Jose Malagon# | 34 | 2086-2091 | |
| 16 | Jayden Thomas# | 33 | 2097-2098 | |
| 17 | Danny Amonett | 32 | 2075-2077 | |
| 17 | Dusty Bowers | 32 | 2086-2089 | |
| 17 | Nick Kime | 32 | 2066-2068 | |
| 17 | Willie Vargas | 32 | 2049-2056 | |
| 21 | Justin Jacome | 31 | 2016-2021 | |
| 21 | Mike Kretchmar# | 31 | 2093-2098 | |
| 21 | Matt McConnell | 31 | 2052-2054 | |
| 21 | Mark Stewman | 31 | 2083-2089 | |
| 25 | Chris Geiger# | 30 | 2093-2098 | |
| 25 | Sal Herrera# | 30 | 2086-2089 | |
| 25 | Mike Jones# | 30 | 2093-2097 | |
| 25 | Amando Ortigueira# | 30 | 2088-2091 | |
| 25 | Mario Velasco# | 30 | 2095-2098 | |
| 30 | Alex Aguilar# | 29 | 2094-2096 | |
| 30 | Francisco Castellanos# | 29 | 2085-2089 | |
| 30 | Nick Hill | 29 | 2050-2055 | |
| 30 | Onpei Murakami | 29 | 2057-2061 | |
| 34 | Tony Aldana | 28 | 2060-2063 | |
| 34 | Bill Caudell# | 28 | 2096-2098 | |
| 34 | Alfredo Guerrero | 28 | 2055-2058 | |
| 34 | Chris McHugh# | 28 | 2096-2098 | |
| 34 | Christian Morris | 28 | 2015-2021 | |
| 34 | Willie Portugal# | 28 | 2096-2098 | |
| 40 | Jeff Adler | 27 | 2049-2050 | |
| 40 | Calvin Carter# | 27 | 2094-2096 | |
| 40 | Terrell Hagans | 27 | 2086-2089 | |
| 40 | Jorge Pichardo | 27 | 2057-2059 | |
| 40 | Frank Riesgo | 27 | 2029-2031 | |
| 40 | Roberto Serrano# | 27 | 2088-2089 | |
| 46 | Sergio Arriola | 26 | 2043-2044 | |
| 46 | Max Klotz | 26 | 2093-2096 | |
| 46 | Kevin Qualls# | 26 | 2092-2095 | |
| 46 | Eric Watson# | 26 | 2092-2093 | |
| 50 | Jeremy Arnold | 25 | 2049-2050 | |
| 50 | Bill Capito | 25 | 2076-2078 | |
| 50 | Andrew Cooke | 25 | 2043-2050 | |
| 50 | Brian Forman | 25 | 2076-2077 | |
| 50 | Andy Losinski# | 25 | 2097-2098 | |
| 50 | Jayden Stephens# | 25 | 2095-2098 | |
| 50 | Jonathan Todd | 25 | 2052-2055 | |
| 57 | Wilfred Colvin# | 24 | 2096-2098 | |
| 57 | Zach Jackson | 24 | 2005-2008 | |
| 57 | Jose Macias | 24 | 2054-2056 | |
| 57 | Moritz Moed | 24 | 2054-2057 | |
| 57 | Sean Moore# | 24 | 2094-2096 | |
| 57 | Danny Strong# | 24 | 2094-2095 | |
| 57 | Bill Whitcomb# | 24 | 2094-2097 | |
| 64 | Jason Chesak | 23 | 2069-2070 | |
| 64 | Victor Costilla# | 23 | 2089-2090 | |
| 64 | Mike Garrett# | 23 | 2088-2091 | |
| 64 | Steve Hanks | 23 | 2065-2067 | |
| 64 | Frank Lieb | 23 | 2044-2057 | |
| 64 | Job MacDonald# | 23 | 2097-2098 | |
| 64 | Angel Portalatin | 23 | 2041-2044 | |
| 64 | Austin Smith | 23 | 2017-2019 | |
| 72 | Travis Bergen | 22 | 2017-2021 | |
| 72 | Juan Briagas | 22 | 2025-2027 | |
| 72 | Marty Cogdill | 22 | 2035-2046 | |
| 72 | Robby Gajda | 22 | 2061-2064 | |
| 72 | Israel Jerez# | 22 | 2094-2096 | |
| 72 | David Lucia# | 22 | 2093-2094 | |
| 72 | Brandon Meyer# | 22 | 2093-2096 | |
| 72 | Carlos Morales | 22 | 2033-2034 | |
| 72 | Alex Moreno | 22 | 2051-2053 | |
| 72 | Tony Perri | 22 | 2068-2069 | |
| 72 | Israel Rios | 22 | 2058-2063 | |
| 72 | Ed Stephenson | 22 | 2028-2030 | |
| 72 | Jaylen Williams | 22 | 2069-2074 | |
| 85 | Jeff Bennett | 21 | 2001-2002 | |
| 85 | Matt Crouse | 21 | 2012-2016 | |
| 85 | Ivan Duran# | 21 | 2088-2094 | |
| 85 | Joel Elizarraraz# | 21 | 2087-2089 | |
| 85 | Zack Gilbert | 21 | 2066-2071 | |
| 85 | Arturo Gutierrez | 21 | 2046-2053 | |
| 85 | Justin Harrington | 21 | 2082-2084 | |
| 85 | Raul Mata | 21 | 2026-2030 | |
| 85 | Ian Merrill | 21 | 2057-2063 | |
| 85 | Dustin Michaud | 21 | 2070-2073 | |
| 85 | Tervell Pierce | 21 | 2082-2083 | |
| 85 | Enrique Rodriguez | 21 | 2056-2058 | |
| 85 | Karl Sibley | 21 | 2084-2085 | |
| 85 | Eric Springfield | 21 | 2085-2091 | |
| 99 | Victor Arano | 20 | 2015-2016 | |
| 99 | Travis Baca# | 20 | 2090-2095 |
