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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Eric Price | 24 | 2017-2020 | |
| 2 | Shawn O'Reilly | 20 | 2039-2042 | |
| 3 | José Manuel | 19 | 2026-2028 | |
| 3 | Joe Miller | 19 | 2021-2023 | |
| 5 | Bob Parker | 18 | 2021-2023 | |
| 5 | Rob Robinson | 18 | 2043-2046 | |
| 7 | Lars-Bjorn Grundvig | 17 | 2017-2020 | |
| 7 | Terence Jackson | 17 | 2029-2031 | |
| 7 | Tetsuhiko Kichida | 17 | 2017-2019 | |
| 7 | Ryan Michelet# | 17 | 2057-2060 | |
| 7 | Curt Peterson | 17 | 2025-2027 | |
| 7 | Mike Powell | 17 | 2018-2020 | |
| 7 | Randy White | 17 | 2017-2020 | |
| 14 | Terrence Beck | 16 | 2024-2026 | |
| 14 | Dana Bolen | 16 | 2017-2020 | |
| 14 | Jim Coker | 16 | 2018-2020 | |
| 14 | Jim Fish | 16 | 2018-2020 | |
| 14 | Bob Grant* | 16 | 2027-2029 | |
| 14 | Devin Holland | 16 | 2019-2021 | |
| 14 | Mike Imes | 16 | 2042-2045 | |
| 14 | Chris Miller | 16 | 2027-2029 | |
| 14 | Jesús Ortega | 16 | 2026-2028 | |
| 14 | Jimmy Sheehan | 16 | 2038-2041 | |
| 14 | Jeff Stephens | 16 | 2018-2020 | |
| 14 | Jon Wiggins# | 16 | 2058-2061 | |
| 14 | Zander Wright | 16 | 2023-2025 | |
| 27 | Manny Aguilar# | 15 | 2058-2062 | |
| 27 | Jake Ashley | 15 | 2026-2028 | |
| 27 | Ed Brooks | 15 | 2025-2027 | |
| 27 | Bill Cosme# | 15 | 2051-2054 | |
| 27 | Alain Cros# | 15 | 2061-2065 | |
| 27 | Ben Dale | 15 | 2021-2023 | |
| 27 | Rubén Ferreira* | 15 | 2018-2020 | |
| 27 | Tommy Green | 15 | 2018-2020 | |
| 27 | Eric King# | 15 | 2042-2045 | |
| 27 | Alfredo Montaño | 15 | 2017-2019 | |
| 27 | Brad Nelson | 15 | 2018-2020 | |
| 27 | Erik Oliver | 15 | 2018-2020 | |
| 27 | César Ramírez | 15 | 2020-2022 | |
| 27 | Jimmy Small | 15 | 2018-2020 | |
| 27 | Eric Turner | 15 | 2022-2024 | |
| 27 | Juan Villanueva | 15 | 2017-2020 | |
| 27 | Steve Vincent* | 15 | 2018-2020 | |
| 27 | Joe Walden# | 15 | 2057-2061 | |
| 27 | Kel Walden | 15 | 2017-2019 | |
| 27 | Bob Walker | 15 | 2041-2044 | |
| 27 | Hoon Yi | 15 | 2033-2035 | |
| 48 | Matt Bates | 14 | 2031-2033 | |
| 48 | Bob Bell | 14 | 2026-2028 | |
| 48 | J.D. Bryant# | 14 | 2057-2061 | |
| 48 | Toby Couch | 14 | 2017-2020 | |
| 48 | Greg Curran | 14 | 2032-2034 | |
| 48 | Mike Dalton | 14 | 2023-2025 | |
| 48 | Greg Goff | 14 | 2019-2021 | |
| 48 | Jose Gonzalez# | 14 | 2059-2063 | |
| 48 | Kevin Gray | 14 | 2039-2042 | |
| 48 | Willie Gutiérrez | 14 | 2029-2031 | |
| 48 | César Hernández | 14 | 2018-2020 | |
| 48 | Gil Kent | 14 | 2020-2022 | |
| 48 | Edmund McCullough | 14 | 2021-2023 | |
| 48 | José Méndez | 14 | 2021-2023 | |
| 48 | Charlie Norton | 14 | 2024-2026 | |
| 48 | Rod O'Colgan Jr. | 14 | 2030-2032 | |
| 48 | Eddie Rhodes | 14 | 2025-2027 | |
| 48 | Jon Swanson | 14 | 2019-2021 | |
| 48 | Jonathan Wilson | 14 | 2026-2028 | |
| 67 | Jeff Amery | 13 | 2039-2042 | |
| 67 | Dennis Carlson# | 13 | 2043-2046 | |
| 67 | Steve Carpenter | 13 | 2041-2044 | |
| 67 | Mike Cox | 13 | 2034-2036 | |
| 67 | Jamie Drake | 13 | 2018-2020 | |
| 67 | Frank Erwin# | 13 | 2058-2062 | |
| 67 | Mario Gonzáles | 13 | 2022-2024 | |
| 67 | Avisa Gutala# | 13 | 2061-2065 | |
| 67 | Jeff Harris | 13 | 2028-2030 | |
| 67 | Lou Harvey# | 13 | 2043-2046 | |
| 67 | Jarred Hill# | 13 | 2043-2046 | |
| 67 | Dave Jennings | 13 | 2018-2020 | |
| 67 | Ed Johnston | 13 | 2022-2024 | |
| 67 | Daryl McCoy | 13 | 2035-2037 | |
| 67 | Steve McIntyre | 13 | 2022-2024 | |
| 67 | Nate Mulholland# | 13 | 2043-2046 | |
| 67 | Jim Mullen | 13 | 2028-2030 | |
| 67 | Curt Reed | 13 | 2020-2022 | |
| 67 | Manuel Schleusingen | 13 | 2024-2026 | |
| 67 | Gil Steele# | 13 | 2049-2052 | |
| 67 | Jerry Sánchez | 13 | 2018-2020 | |
| 67 | Robert Thurston# | 13 | 2057-2061 | |
| 67 | Orlando Trejo | 13 | 2040-2043 | |
| 67 | Johnny Washington | 13 | 2024-2026 | |
| 67 | Bobby Young | 13 | 2033-2035 | |
| 92 | Loren Ames | 12 | 2021-2023 | |
| 92 | Edgardo Bernard | 12 | 2029-2031 | |
| 92 | Ron Davis | 12 | 2021-2023 | |
| 92 | Daniel Durand# | 12 | 2057-2061 | |
| 92 | Pedro Fernandez# | 12 | 2060-2064 | |
| 92 | Jon Francis | 12 | 2032-2034 | |
| 92 | Bob Gilbert | 12 | 2026-2028 | |
| 92 | Keagan Gill | 12 | 2023-2025 | |
| 92 | Jim Graham | 12 | 2042-2045 |
