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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Izzy Marquez | 310 | 2027-2047 | |
| 2 | Juan Gonzalez# | 276 | 2033-2048 | |
| 3 | Kevin Choate* | 272 | 2018-2033 | |
| 4 | Brad Riddick# | 219 | 2033-2048 | |
| 5 | Mike Ellis | 209 | 2019-2036 | |
| 6 | Jason Sumrall | 208 | 2023-2042 | |
| 7 | Kwan-wuk Tae# | 202 | 2034-2048 | |
| 8 | Steve Thomas# | 200 | 2030-2048 | |
| 9 | Scott Drum* | 197 | 2028-2040 | |
| 10 | Jonathan Romero | 194 | 2019-2035 | |
| 11 | Justin Carrillo | 189 | 2025-2041 | |
| 11 | Mike Rensi | 189 | 2021-2036 | |
| 13 | Steven Allen | 186 | 2030-2044 | |
| 13 | Tom Call | 186 | 2032-2047 | |
| 13 | Karl Gordam# | 186 | 2040-2048 | |
| 16 | Mike Storbeck | 185 | 2031-2047 | |
| 17 | Ryan Morales | 183 | 2025-2039 | |
| 18 | Oscar Bribiesca | 169 | 2018-2031 | |
| 18 | John Hoover# | 169 | 2032-2048 | |
| 20 | Adam Dodson# | 168 | 2035-2048 | |
| 21 | Jared Marks | 165 | 2018-2028 | |
| 21 | Sergio Nunez# | 165 | 2034-2048 | |
| 21 | Dan O'Keeffe | 165 | 2030-2045 | |
| 21 | Bill Rich | 165 | 2030-2045 | |
| 25 | Ricardo Baena | 164 | 2022-2034 | |
| 26 | Ricky Castillo | 162 | 2028-2044 | |
| 26 | Kevin Feltes# | 162 | 2037-2048 | |
| 26 | Steve Gorter | 162 | 2030-2045 | |
| 29 | Dave Adams | 160 | 2031-2046 | |
| 30 | Mark Foglesong# | 159 | 2035-2048 | |
| 30 | John Williams | 159 | 2021-2039 | |
| 32 | Jason Mosier | 158 | 2023-2035 | |
| 33 | Eric Casale# | 157 | 2031-2048 | |
| 34 | Joe Miller | 155 | 2025-2039 | |
| 34 | Josh Pierce# | 155 | 2036-2048 | |
| 36 | Seth Chewning | 152 | 2018-2033 | |
| 37 | Eric Adamonis# | 150 | 2030-2048 | |
| 37 | Efrain Gonzalez | 150 | 2025-2040 | |
| 39 | Bryce Kelly | 149 | 2023-2037 | |
| 40 | Brian Collins# | 148 | 2035-2048 | |
| 41 | Donald Burroughs | 145 | 2018-2029 | |
| 42 | Dave Christensen | 143 | 2018-2028 | |
| 42 | Toby Guinn# | 143 | 2038-2048 | |
| 42 | Ryan Milana | 143 | 2022-2036 | |
| 45 | Peter Mgulia | 140 | 2032-2044 | |
| 46 | Jose Moreno | 139 | 2018-2030 | |
| 46 | Alan Scafidi | 139 | 2023-2034 | |
| 46 | Jake Turner | 139 | 2029-2046 | |
| 49 | Dan Coffman# | 137 | 2034-2048 | |
| 50 | Neil Bryan | 136 | 2024-2038 | |
| 50 | Vinny Zavala | 136 | 2033-2045 | |
| 52 | Craig Simon | 135 | 2029-2040 | |
| 53 | Jeremy Myers# | 134 | 2036-2048 | |
| 54 | Jeff Johnson | 133 | 2018-2028 | |
| 55 | Allen George | 132 | 2018-2028 | |
| 56 | Mike Pentland | 131 | 2031-2045 | |
| 57 | Rick Santy | 130 | 2031-2043 | |
| 57 | Miklas van Gool | 130 | 2026-2043 | |
| 59 | Aaron Whittle | 129 | 2030-2043 | |
| 60 | Jamie Kirchner | 128 | 2027-2046 | |
| 60 | Sam Mooney# | 128 | 2040-2048 | |
| 60 | Melvin Verdin# | 128 | 2033-2048 | |
| 63 | John Nimmo | 125 | 2019-2030 | |
| 64 | Luis Cantu | 123 | 2019-2032 | |
| 64 | Ivan Hassett | 123 | 2033-2044 | |
| 66 | Jim Steeb# | 121 | 2034-2048 | |
| 67 | Siu-chung Chieu# | 120 | 2034-2048 | |
| 68 | Matt Robertson | 116 | 2029-2043 | |
| 68 | David Ward | 116 | 2026-2036 | |
| 70 | Darren Manos | 114 | 2033-2043 | |
| 71 | Rich Montgomery | 113 | 2031-2043 | |
| 71 | Justin Petro | 113 | 2021-2034 | |
| 73 | Jason Stueck | 112 | 2018-2027 | |
| 74 | Henry Flores# | 111 | 2038-2048 | |
| 75 | Bryce DeMont | 110 | 2018-2028 | |
| 75 | Faddei Madaev | 110 | 2028-2040 | |
| 77 | Jose Giminez# | 109 | 2033-2048 | |
| 78 | Danny Garcia | 108 | 2018-2025 | |
| 78 | Mike Stefanik | 108 | 2023-2035 | |
| 80 | Ramon Jacquez# | 107 | 2033-2048 | |
| 81 | Joey Frank | 104 | 2027-2042 | |
| 82 | Jordan Canales | 102 | 2025-2037 | |
| 82 | Ivan Ceballo# | 102 | 2036-2047 | |
| 82 | Jerry Griffiths | 102 | 2025-2039 | |
| 85 | Miguel Cruz | 100 | 2021-2031 | |
| 85 | Mat Thornton | 100 | 2025-2038 | |
| 87 | Seung-hyeon Kim | 99 | 2022-2032 | |
| 87 | J.J. Mason | 99 | 2034-2044 | |
| 89 | Matt Gunnison# | 98 | 2030-2048 | |
| 89 | Marco Pagan# | 98 | 2033-2048 | |
| 91 | Mike Rodriguez# | 97 | 2039-2048 | |
| 92 | David Beres | 96 | 2018-2028 | |
| 92 | Fred Gibson | 96 | 2033-2043 | |
| 92 | Kevin Lowe# | 96 | 2033-2048 | |
| 92 | Brent Page# | 96 | 2034-2047 | |
| 92 | Mike Thames | 96 | 2020-2029 | |
| 97 | Ernesto de la Pena | 93 | 2018-2028 | |
| 97 | Oren Murry# | 93 | 2037-2047 | |
| 97 | Josh Reed | 93 | 2031-2044 | |
| 100 | Wil Calvo | 91 | 2026-2040 |
