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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Gonzalez# | 315 | 2033-2052 | |
| 2 | Izzy Marquez* | 310 | 2027-2047 | |
| 3 | Kevin Choate* | 272 | 2018-2033 | |
| 4 | Brad Riddick# | 247 | 2033-2051 | |
| 5 | Kwan-wuk Tae# | 234 | 2034-2052 | |
| 6 | Karl Gordam# | 217 | 2040-2052 | |
| 7 | John Hoover# | 215 | 2032-2052 | |
| 8 | Steve Thomas | 210 | 2030-2049 | |
| 9 | Mike Ellis | 209 | 2019-2036 | |
| 10 | Jason Sumrall | 208 | 2023-2042 | |
| 11 | Scott Drum* | 197 | 2028-2040 | |
| 12 | Jonathan Romero | 194 | 2019-2035 | |
| 13 | Justin Carrillo | 189 | 2025-2041 | |
| 13 | Mike Rensi | 189 | 2021-2036 | |
| 15 | Steven Allen | 186 | 2030-2044 | |
| 15 | Tom Call | 186 | 2032-2047 | |
| 17 | Mike Storbeck* | 185 | 2031-2047 | |
| 18 | Mark Foglesong# | 183 | 2035-2051 | |
| 18 | Ryan Morales | 183 | 2025-2039 | |
| 20 | Brian Collins# | 181 | 2035-2052 | |
| 21 | Adam Dodson | 180 | 2035-2051 | |
| 22 | Kevin Feltes# | 177 | 2037-2052 | |
| 23 | Toby Guinn# | 171 | 2038-2052 | |
| 24 | Oscar Bribiesca | 169 | 2018-2031 | |
| 25 | Jared Marks | 165 | 2018-2028 | |
| 25 | Sergio Nunez | 165 | 2034-2048 | |
| 25 | Dan O'Keeffe | 165 | 2030-2045 | |
| 25 | Bill Rich | 165 | 2030-2045 | |
| 29 | Ricardo Baena | 164 | 2022-2034 | |
| 30 | Eric Adamonis | 162 | 2030-2049 | |
| 30 | Eric Casale | 162 | 2031-2050 | |
| 30 | Ricky Castillo | 162 | 2028-2044 | |
| 30 | Steve Gorter | 162 | 2030-2045 | |
| 34 | Jeremy Myers# | 161 | 2036-2051 | |
| 35 | Dave Adams | 160 | 2031-2046 | |
| 36 | John Williams | 159 | 2021-2039 | |
| 37 | Jason Mosier | 158 | 2023-2035 | |
| 38 | Joe Miller | 155 | 2025-2039 | |
| 38 | Josh Pierce | 155 | 2036-2048 | |
| 40 | Sam Mooney# | 153 | 2040-2052 | |
| 41 | Seth Chewning | 152 | 2018-2033 | |
| 42 | Efrain Gonzalez | 150 | 2025-2040 | |
| 43 | Bryce Kelly | 149 | 2023-2037 | |
| 44 | Donald Burroughs | 145 | 2018-2029 | |
| 45 | Dave Christensen | 143 | 2018-2028 | |
| 45 | Ryan Milana | 143 | 2022-2036 | |
| 47 | Dan Coffman | 142 | 2034-2049 | |
| 48 | Peter Mgulia | 140 | 2032-2044 | |
| 48 | Jim Steeb# | 140 | 2034-2051 | |
| 50 | Jose Moreno | 139 | 2018-2030 | |
| 50 | Alan Scafidi | 139 | 2023-2034 | |
| 50 | Jake Turner | 139 | 2029-2046 | |
| 53 | Neil Bryan | 136 | 2024-2038 | |
| 53 | Vinny Zavala | 136 | 2033-2045 | |
| 55 | Spencer Hay# | 135 | 2042-2052 | |
| 55 | Craig Simon | 135 | 2029-2040 | |
| 57 | Jeff Johnson | 133 | 2018-2028 | |
| 58 | Allen George | 132 | 2018-2028 | |
| 59 | Mike Pentland | 131 | 2031-2045 | |
| 60 | Rick Santy | 130 | 2031-2043 | |
| 60 | Miklas van Gool | 130 | 2026-2043 | |
| 62 | Aaron Whittle | 129 | 2030-2043 | |
| 63 | Jamie Kirchner | 128 | 2027-2046 | |
| 63 | Melvin Verdin | 128 | 2033-2048 | |
| 65 | John Nimmo | 125 | 2019-2030 | |
| 66 | Luis Cantu | 123 | 2019-2032 | |
| 66 | Ivan Hassett | 123 | 2033-2044 | |
| 68 | Siu-chung Chieu | 120 | 2034-2048 | |
| 68 | Billy Roland# | 120 | 2038-2052 | |
| 70 | Matt Robertson | 116 | 2029-2043 | |
| 70 | David Ward | 116 | 2026-2036 | |
| 72 | Darren Manos | 114 | 2033-2043 | |
| 73 | Jose Giminez | 113 | 2033-2049 | |
| 73 | Ramon Jacquez | 113 | 2033-2050 | |
| 73 | Rich Montgomery | 113 | 2031-2043 | |
| 73 | Justin Petro | 113 | 2021-2034 | |
| 73 | Andy Pittman# | 113 | 2043-2052 | |
| 73 | Mike Rodriguez# | 113 | 2039-2051 | |
| 79 | Jason Stueck | 112 | 2018-2027 | |
| 80 | Henry Flores | 111 | 2038-2048 | |
| 80 | Marco Pagan | 111 | 2033-2050 | |
| 82 | Bryce DeMont | 110 | 2018-2028 | |
| 82 | Faddei Madaev | 110 | 2028-2040 | |
| 84 | Mike Ricketts# | 109 | 2043-2052 | |
| 85 | Danny Garcia | 108 | 2018-2025 | |
| 85 | Mike Stefanik | 108 | 2023-2035 | |
| 87 | Joey Frank | 104 | 2027-2042 | |
| 88 | Jordan Canales | 102 | 2025-2037 | |
| 88 | Ivan Ceballo | 102 | 2036-2048 | |
| 88 | Jerry Griffiths | 102 | 2025-2039 | |
| 91 | Miguel Cruz | 100 | 2021-2031 | |
| 91 | Mat Thornton | 100 | 2025-2038 | |
| 93 | Matt Gunnison | 99 | 2030-2049 | |
| 93 | Rourke Ireland | 99 | 2032-2049 | |
| 93 | Seung-hyeon Kim | 99 | 2022-2032 | |
| 93 | J.J. Mason | 99 | 2034-2044 | |
| 97 | Kevin Lowe | 97 | 2033-2049 | |
| 97 | Alejandro Rodriguez# | 97 | 2041-2050 | |
| 99 | David Beres | 96 | 2018-2028 | |
| 99 | Fred Gibson | 96 | 2033-2043 |
