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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Kevin Choate* | 272 | 2018-2033 | |
| 2 | Izzy Marquez# | 247 | 2027-2041 | |
| 3 | Mike Ellis | 209 | 2019-2036 | |
| 4 | Jason Sumrall# | 206 | 2023-2041 | |
| 5 | Scott Drum | 197 | 2028-2040 | |
| 6 | Jonathan Romero | 194 | 2019-2035 | |
| 7 | Justin Carrillo | 189 | 2025-2041 | |
| 7 | Mike Rensi | 189 | 2021-2036 | |
| 9 | Ryan Morales | 183 | 2025-2039 | |
| 10 | Oscar Bribiesca | 169 | 2018-2031 | |
| 11 | Jared Marks | 165 | 2018-2028 | |
| 12 | Ricardo Baena | 164 | 2022-2034 | |
| 13 | Ricky Castillo# | 161 | 2028-2041 | |
| 14 | Juan Gonzalez# | 159 | 2033-2041 | |
| 14 | John Williams | 159 | 2021-2039 | |
| 16 | Jason Mosier | 158 | 2023-2035 | |
| 17 | Steven Allen# | 157 | 2030-2041 | |
| 18 | Joe Miller | 155 | 2025-2039 | |
| 19 | Seth Chewning | 152 | 2018-2033 | |
| 19 | Mike Storbeck# | 152 | 2031-2041 | |
| 21 | Efrain Gonzalez | 150 | 2025-2040 | |
| 22 | Bryce Kelly | 149 | 2023-2037 | |
| 23 | Donald Burroughs | 145 | 2018-2029 | |
| 24 | Dave Christensen | 143 | 2018-2028 | |
| 24 | Ryan Milana | 143 | 2022-2036 | |
| 26 | Jose Moreno | 139 | 2018-2030 | |
| 26 | Alan Scafidi | 139 | 2023-2034 | |
| 28 | Dan O'Keeffe# | 138 | 2030-2041 | |
| 29 | Neil Bryan | 136 | 2024-2038 | |
| 30 | Eric Casale# | 135 | 2031-2040 | |
| 30 | Craig Simon | 135 | 2029-2040 | |
| 32 | Tom Call# | 134 | 2032-2041 | |
| 33 | Jeff Johnson | 133 | 2018-2028 | |
| 34 | Allen George | 132 | 2018-2028 | |
| 34 | Bill Rich# | 132 | 2030-2041 | |
| 36 | Steve Gorter# | 130 | 2030-2041 | |
| 37 | Brad Riddick# | 129 | 2033-2041 | |
| 38 | Steve Thomas# | 127 | 2030-2041 | |
| 38 | Miklas van Gool# | 127 | 2026-2041 | |
| 40 | John Nimmo | 125 | 2019-2030 | |
| 41 | Luis Cantu | 123 | 2019-2032 | |
| 42 | Dave Adams# | 120 | 2031-2041 | |
| 43 | Rick Santy# | 117 | 2031-2041 | |
| 44 | David Ward | 116 | 2026-2036 | |
| 45 | Justin Petro | 113 | 2021-2034 | |
| 46 | Jamie Kirchner# | 112 | 2027-2041 | |
| 46 | Jason Stueck | 112 | 2018-2027 | |
| 48 | Bryce DeMont | 110 | 2018-2028 | |
| 48 | Faddei Madaev# | 110 | 2028-2040 | |
| 48 | Matt Robertson# | 110 | 2029-2041 | |
| 51 | Danny Garcia | 108 | 2018-2025 | |
| 51 | Peter Mgulia# | 108 | 2032-2041 | |
| 51 | Mike Pentland# | 108 | 2031-2041 | |
| 51 | Mike Stefanik | 108 | 2023-2035 | |
| 55 | Sergio Nunez# | 106 | 2034-2041 | |
| 56 | Joey Frank# | 104 | 2027-2041 | |
| 57 | Rich Montgomery# | 103 | 2031-2041 | |
| 58 | Jordan Canales | 102 | 2025-2037 | |
| 58 | Jerry Griffiths | 102 | 2025-2039 | |
| 58 | Aaron Whittle# | 102 | 2030-2041 | |
| 61 | Miguel Cruz | 100 | 2021-2031 | |
| 61 | Kwan-wuk Tae# | 100 | 2034-2041 | |
| 61 | Mat Thornton | 100 | 2025-2038 | |
| 64 | Seung-hyeon Kim | 99 | 2022-2032 | |
| 64 | Vinny Zavala# | 99 | 2033-2041 | |
| 66 | John Hoover# | 98 | 2032-2041 | |
| 66 | Darren Manos# | 98 | 2033-2041 | |
| 68 | David Beres | 96 | 2018-2028 | |
| 68 | Adam Dodson# | 96 | 2035-2041 | |
| 68 | Mike Thames | 96 | 2020-2029 | |
| 71 | Jake Turner# | 94 | 2029-2041 | |
| 72 | Ernesto de la Pena | 93 | 2018-2028 | |
| 73 | Wil Calvo | 91 | 2026-2040 | |
| 74 | Alexei Liberman# | 90 | 2029-2040 | |
| 75 | Daniel Cuevas | 88 | 2018-2028 | |
| 76 | Allen Elkins | 86 | 2026-2039 | |
| 77 | Fred Gibson# | 84 | 2033-2041 | |
| 78 | Eric Bonner | 83 | 2018-2026 | |
| 78 | Dustin Swiercz# | 83 | 2031-2040 | |
| 80 | Pat Dudding | 82 | 2026-2035 | |
| 80 | Mark Foglesong# | 82 | 2035-2041 | |
| 82 | Eric Adamonis# | 81 | 2030-2041 | |
| 82 | Brad Brummel# | 81 | 2031-2041 | |
| 84 | Ivan Hassett# | 80 | 2033-2041 | |
| 84 | Kevin Kress# | 80 | 2032-2040 | |
| 86 | Jorge Lujan# | 79 | 2029-2041 | |
| 87 | Gary Gemmill# | 78 | 2031-2041 | |
| 87 | Alexis Mendez* | 78 | 2018-2034 | |
| 87 | Pete Miller | 78 | 2020-2030 | |
| 87 | Josh Pierce# | 78 | 2036-2041 | |
| 91 | Brian Collins# | 77 | 2035-2041 | |
| 91 | Josh Reed# | 77 | 2031-2041 | |
| 91 | Melvin Verdin# | 77 | 2033-2041 | |
| 94 | Lawrence Dupree | 76 | 2023-2032 | |
| 95 | Gerardo Cruz | 75 | 2018-2025 | |
| 95 | J.J. Mason# | 75 | 2034-2041 | |
| 95 | Kevin Troughton | 75 | 2018-2025 | |
| 98 | Andrew Carroll# | 74 | 2025-2041 | |
| 98 | Phil Prat | 74 | 2018-2026 | |
| 100 | Matt Hummel | 73 | 2018-2023 |
