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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Max Grant | 6 | 2019-2034 | |
| 2 | Tom Collins | 4 | 2017-2026 | |
| 2 | Grant Huffman | 4 | 2032-2035 | |
| 2 | Fernando Vazquez# | 4 | 2052-2052 | |
| 2 | Paul Woodrow | 4 | 2023-2025 | |
| 6 | Kenny Balch | 3 | 2045-2045 | |
| 6 | Leland Bullins | 3 | 2030-2033 | |
| 6 | Casey Etheredge# | 3 | 2057-2057 | |
| 6 | Elijah Gourdine# | 3 | 2057-2060 | |
| 6 | Larry Greer | 3 | 2028-2030 | |
| 6 | Randy Hamilton | 3 | 2015-2015 | |
| 6 | Dusty Harvat | 3 | 2044-2047 | |
| 6 | Sam Hatt | 3 | 2021-2022 | |
| 6 | John Hunter# | 3 | 2057-2060 | |
| 6 | Reagan Juneau | 3 | 2040-2042 | |
| 6 | Barrett Lamb | 3 | 2030-2040 | |
| 6 | Mançio Madrra# | 3 | 2060-2060 | |
| 6 | Gabin Martin | 3 | 2024-2026 | |
| 6 | Matt Nolan | 3 | 2028-2034 | |
| 6 | Mike Olejarz# | 3 | 2059-2060 | |
| 6 | Eisuke Ota | 3 | 2026-2026 | |
| 6 | Kichibei Ozawa | 3 | 2024-2025 | |
| 6 | Jose Patino# | 3 | 2048-2054 | |
| 6 | Jake Robinson | 3 | 2017-2027 | |
| 6 | Joel Stapleton | 3 | 2035-2040 | |
| 6 | Kyle Taylor# | 3 | 2054-2057 | |
| 6 | Alfredo Tirado | 3 | 2050-2053 | |
| 6 | Manny Villalobos | 3 | 2043-2046 | |
| 6 | António Vélez | 3 | 2014-2019 | |
| 6 | Jon Wambach# | 3 | 2058-2060 | |
| 6 | David White | 3 | 2015-2023 | |
| 6 | Fei-hsien Xun | 3 | 2043-2046 | |
| 33 | Todd Anderson | 2 | 2028-2031 | |
| 33 | Baltwin Baars | 2 | 2023-2024 | |
| 33 | Henry Baker | 2 | 2035-2044 | |
| 33 | Ted Baker# | 2 | 2049-2053 | |
| 33 | Trevor Biggs | 2 | 2048-2051 | |
| 33 | Stéphane Blin | 2 | 2015-2019 | |
| 33 | Ben Butler | 2 | 2048-2053 | |
| 33 | George Cain | 2 | 2043-2044 | |
| 33 | Josh Caldwell | 2 | 2047-2049 | |
| 33 | Pedro Cerna | 2 | 2037-2041 | |
| 33 | Chuk-yan Chio | 2 | 2021-2028 | |
| 33 | Cliff Clark | 2 | 2012-2012 | |
| 33 | Justin Dolan# | 2 | 2058-2060 | |
| 33 | Dave Dyke | 2 | 2034-2041 | |
| 33 | Kichibei Endo | 2 | 2028-2031 | |
| 33 | Alfonso Espinoza | 2 | 2043-2043 | |
| 33 | Daryl Feaviour | 2 | 2022-2023 | |
| 33 | D.J. Fisher | 2 | 2050-2053 | |
| 33 | Cecilio Friuli | 2 | 2029-2041 | |
| 33 | Pedro Galló | 2 | 2031-2033 | |
| 33 | Josh Geary | 2 | 2056-2059 | |
| 33 | Javier González | 2 | 2029-2033 | |
| 33 | David Guyer | 2 | 2036-2037 | |
| 33 | Tom Hanson | 2 | 2021-2027 | |
| 33 | Zach Hensler | 2 | 2035-2042 | |
| 33 | Bobby Holguin | 2 | 2049-2050 | |
| 33 | Charlie Hopkins | 2 | 2013-2025 | |
| 33 | Joe Hull | 2 | 2045-2047 | |
| 33 | Shojiro Inoue | 2 | 2024-2029 | |
| 33 | John Jacobs | 2 | 2018-2019 | |
| 33 | Ricardo Jarquin | 2 | 2038-2044 | |
| 33 | Roger Katz | 2 | 2037-2045 | |
| 33 | Ijaz Kharoti | 2 | 2024-2039 | |
| 33 | Harold Lane | 2 | 2039-2047 | |
| 33 | Bobby Lloyd | 2 | 2034-2037 | |
| 33 | Oscar Lopez# | 2 | 2055-2056 | |
| 33 | Bryan Lynch | 2 | 2022-2023 | |
| 33 | José López | 2 | 2034-2034 | |
| 33 | Clive Macaulay | 2 | 2034-2037 | |
| 33 | Manuel Marroquín | 2 | 2017-2021 | |
| 33 | Saiyid Mashwanis | 2 | 2027-2028 | |
| 33 | Pat McConnell | 2 | 2028-2028 | |
| 33 | Dave McCrudden | 2 | 2036-2037 | |
| 33 | Charlie McDermott | 2 | 2045-2046 | |
| 33 | Joe McKnight# | 2 | 2053-2055 | |
| 33 | A.J. Meier# | 2 | 2051-2053 | |
| 33 | Frazer Morrison | 2 | 2043-2047 | |
| 33 | Dave Munier | 2 | 2030-2032 | |
| 33 | Dwight Munroe | 2 | 2049-2051 | |
| 33 | Yukihiro Nakamoto | 2 | 2033-2041 | |
| 33 | Tore O'Brien | 2 | 2046-2046 | |
| 33 | Aaron O'Donnell | 2 | 2046-2048 | |
| 33 | Kulapati Pandian | 2 | 2019-2021 | |
| 33 | Travis Panhorst | 2 | 2036-2040 | |
| 33 | Benjamin Piece | 2 | 2026-2038 | |
| 33 | Dave Pinkley | 2 | 2040-2043 | |
| 33 | Kyle Ragsdale | 2 | 2048-2049 | |
| 33 | Jayakar Ramadin | 2 | 2020-2028 | |
| 33 | Nelson Ramirez# | 2 | 2056-2057 | |
| 33 | David Rios | 2 | 2039-2043 | |
| 33 | Pedro Rosário | 2 | 2016-2020 | |
| 33 | Robby Shea | 2 | 2056-2059 | |
| 33 | Kirk Snyder | 2 | 2012-2015 | |
| 33 | Morihiro Sugano# | 2 | 2050-2056 | |
| 33 | Javier Sánchez | 2 | 2034-2040 | |
| 33 | Nick Tartaglione | 2 | 2049-2050 | |
| 33 | Nelson Taylor | 2 | 2012-2012 | |
| 33 | Divyaprabhava Utpat | 2 | 2045-2046 |
