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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# | 285 | 2033-2049 | |
| 3 | Kevin Choate* | 272 | 2018-2033 | |
| 4 | Brad Riddick# | 227 | 2033-2049 | |
| 5 | Kwan-wuk Tae# | 211 | 2034-2049 | |
| 6 | Mike Ellis | 209 | 2019-2036 | |
| 7 | Jason Sumrall | 208 | 2023-2042 | |
| 7 | Steve Thomas# | 208 | 2030-2049 | |
| 9 | Scott Drum* | 197 | 2028-2040 | |
| 10 | Jonathan Romero | 194 | 2019-2035 | |
| 11 | Karl Gordam# | 191 | 2040-2049 | |
| 12 | Justin Carrillo | 189 | 2025-2041 | |
| 12 | Mike Rensi | 189 | 2021-2036 | |
| 14 | Steven Allen | 186 | 2030-2044 | |
| 14 | Tom Call | 186 | 2032-2047 | |
| 16 | Mike Storbeck | 185 | 2031-2047 | |
| 17 | Ryan Morales | 183 | 2025-2039 | |
| 18 | John Hoover# | 178 | 2032-2049 | |
| 19 | Adam Dodson# | 176 | 2035-2049 | |
| 20 | Kevin Feltes# | 171 | 2037-2049 | |
| 21 | Oscar Bribiesca | 169 | 2018-2031 | |
| 22 | Jared Marks | 165 | 2018-2028 | |
| 22 | Sergio Nunez | 165 | 2034-2048 | |
| 22 | Dan O'Keeffe | 165 | 2030-2045 | |
| 22 | Bill Rich | 165 | 2030-2045 | |
| 26 | Ricardo Baena | 164 | 2022-2034 | |
| 26 | Mark Foglesong# | 164 | 2035-2049 | |
| 28 | Ricky Castillo | 162 | 2028-2044 | |
| 28 | Steve Gorter | 162 | 2030-2045 | |
| 30 | Eric Adamonis# | 160 | 2030-2049 | |
| 30 | Dave Adams | 160 | 2031-2046 | |
| 32 | John Williams | 159 | 2021-2039 | |
| 33 | Jason Mosier | 158 | 2023-2035 | |
| 34 | Eric Casale# | 157 | 2031-2049 | |
| 35 | Brian Collins# | 156 | 2035-2049 | |
| 36 | Joe Miller | 155 | 2025-2039 | |
| 36 | Josh Pierce# | 155 | 2036-2048 | |
| 38 | Seth Chewning | 152 | 2018-2033 | |
| 39 | Efrain Gonzalez | 150 | 2025-2040 | |
| 40 | Bryce Kelly | 149 | 2023-2037 | |
| 41 | Toby Guinn# | 148 | 2038-2049 | |
| 42 | Donald Burroughs | 145 | 2018-2029 | |
| 43 | Dave Christensen | 143 | 2018-2028 | |
| 43 | Ryan Milana | 143 | 2022-2036 | |
| 45 | Dan Coffman# | 140 | 2034-2049 | |
| 45 | Peter Mgulia | 140 | 2032-2044 | |
| 47 | Jose Moreno | 139 | 2018-2030 | |
| 47 | Alan Scafidi | 139 | 2023-2034 | |
| 47 | Jake Turner | 139 | 2029-2046 | |
| 50 | Jeremy Myers# | 138 | 2036-2049 | |
| 51 | Neil Bryan | 136 | 2024-2038 | |
| 51 | Sam Mooney# | 136 | 2040-2049 | |
| 51 | Vinny Zavala | 136 | 2033-2045 | |
| 54 | Craig Simon | 135 | 2029-2040 | |
| 55 | Jeff Johnson | 133 | 2018-2028 | |
| 56 | Allen George | 132 | 2018-2028 | |
| 57 | Mike Pentland | 131 | 2031-2045 | |
| 58 | Rick Santy | 130 | 2031-2043 | |
| 58 | Miklas van Gool | 130 | 2026-2043 | |
| 60 | Aaron Whittle | 129 | 2030-2043 | |
| 61 | Jamie Kirchner | 128 | 2027-2046 | |
| 61 | Melvin Verdin# | 128 | 2033-2048 | |
| 63 | Jim Steeb# | 126 | 2034-2049 | |
| 64 | John Nimmo | 125 | 2019-2030 | |
| 65 | Luis Cantu | 123 | 2019-2032 | |
| 65 | Ivan Hassett | 123 | 2033-2044 | |
| 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 | Jose Giminez# | 113 | 2033-2049 | |
| 71 | Rich Montgomery | 113 | 2031-2043 | |
| 71 | Justin Petro | 113 | 2021-2034 | |
| 74 | Ramon Jacquez# | 112 | 2033-2049 | |
| 74 | Jason Stueck | 112 | 2018-2027 | |
| 76 | Henry Flores# | 111 | 2038-2048 | |
| 77 | Bryce DeMont | 110 | 2018-2028 | |
| 77 | Faddei Madaev | 110 | 2028-2040 | |
| 79 | Danny Garcia | 108 | 2018-2025 | |
| 79 | Mike Stefanik | 108 | 2023-2035 | |
| 81 | Joey Frank | 104 | 2027-2042 | |
| 82 | Jordan Canales | 102 | 2025-2037 | |
| 82 | Ivan Ceballo | 102 | 2036-2048 | |
| 82 | Jerry Griffiths | 102 | 2025-2039 | |
| 85 | Mike Rodriguez# | 101 | 2039-2049 | |
| 86 | Miguel Cruz | 100 | 2021-2031 | |
| 86 | Marco Pagan# | 100 | 2033-2049 | |
| 86 | Mat Thornton | 100 | 2025-2038 | |
| 89 | Matt Gunnison# | 99 | 2030-2049 | |
| 89 | Seung-hyeon Kim | 99 | 2022-2032 | |
| 89 | J.J. Mason | 99 | 2034-2044 | |
| 92 | Kevin Lowe# | 97 | 2033-2049 | |
| 93 | David Beres | 96 | 2018-2028 | |
| 93 | Fred Gibson | 96 | 2033-2043 | |
| 93 | Brent Page# | 96 | 2034-2047 | |
| 93 | Mike Thames | 96 | 2020-2029 | |
| 97 | Ernesto de la Pena | 93 | 2018-2028 | |
| 97 | Rourke Ireland# | 93 | 2032-2049 | |
| 97 | Oren Murry | 93 | 2037-2047 | |
| 97 | Josh Reed | 93 | 2031-2044 |
