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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Alan Alexander Anderson* | 335 | 2020-2038 | |
| 2 | Jimmy Wagner* | 331 | 2025-2046 | |
| 3 | Eddie Batista# | 311 | 2046-2065 | |
| 4 | Kenji Sato# | 310 | 2046-2065 | |
| 5 | Paul Thompson# | 281 | 2046-2065 | |
| 6 | Richard Dicks, Jr.* | 277 | 2019-2036 | |
| 7 | Michael Martin* | 270 | 2030-2048 | |
| 8 | Michael Kilbane* | 266 | 2030-2049 | |
| 9 | Billy Lynch* | 264 | 2034-2052 | |
| 10 | Richard Nagy* | 261 | 2040-2058 | |
| 11 | Brock Vinci* | 255 | 2027-2045 | |
| 12 | Ross Brooks | 253 | 2020-2039 | |
| 13 | Joe Tarnowsky* | 251 | 2025-2040 | |
| 14 | Michael Knox* | 248 | 2031-2048 | |
| 15 | Corey Hicks# | 245 | 2048-2065 | |
| 16 | Mark Cochran* | 244 | 2045-2061 | |
| 17 | Pedro Delgado* | 242 | 2041-2061 | |
| 18 | Oki Okada* | 241 | 2019-2032 | |
| 19 | Bennie Silva | 239 | 2044-2061 | |
| 19 | Mark Sipp* | 239 | 2046-2061 | |
| 21 | David Virgil* | 232 | 2038-2057 | |
| 22 | Timothy Williams | 231 | 2024-2041 | |
| 23 | Michael Gambino* | 228 | 2019-2034 | |
| 23 | Chris Morales | 228 | 2033-2051 | |
| 25 | Francisco Martinez | 227 | 2025-2044 | |
| 26 | Wilson Castillo* | 226 | 2045-2060 | |
| 26 | Marc Jackson* | 226 | 2042-2060 | |
| 28 | Leroy Burbach* | 223 | 2042-2058 | |
| 29 | Manuel Cabrera* | 222 | 2026-2046 | |
| 29 | Christopher Laux | 222 | 2039-2054 | |
| 29 | Pierce Ryan | 222 | 2028-2045 | |
| 32 | Ricardo Camacho* | 221 | 2029-2047 | |
| 33 | Casey Barker* | 220 | 2025-2042 | |
| 34 | Vinny Corleone* | 217 | 2019-2032 | |
| 34 | Harlan Grant* | 217 | 2045-2062 | |
| 36 | William Branch* | 216 | 2045-2061 | |
| 36 | Clinton Keene# | 216 | 2052-2065 | |
| 38 | Keith Patterson* | 215 | 2024-2045 | |
| 39 | Arturo Martinez# | 212 | 2052-2065 | |
| 39 | Tommy Viola | 212 | 2041-2056 | |
| 41 | Burton Bailey | 210 | 2046-2060 | |
| 41 | Fernando Martinez | 210 | 2026-2041 | |
| 43 | Jimmy Dietz* | 209 | 2031-2047 | |
| 44 | Keith Barton* | 205 | 2046-2061 | |
| 45 | Kevin Schmidt | 204 | 2026-2040 | |
| 46 | Ken Hunter* | 203 | 2044-2059 | |
| 47 | Gavin Kane | 202 | 2044-2059 | |
| 47 | Alan Walker | 202 | 2043-2059 | |
| 49 | Millard Hahn# | 201 | 2049-2065 | |
| 50 | Bobby Bruno* | 200 | 2019-2030 | |
| 50 | Aaron Campos# | 200 | 2049-2065 | |
| 52 | Jack Callahan | 199 | 2027-2043 | |
| 52 | Julian Escobar# | 199 | 2053-2065 | |
| 52 | Rafael Morales | 199 | 2026-2041 | |
| 55 | Bo Ford | 198 | 2043-2056 | |
| 55 | Brandon Reynolds | 198 | 2038-2055 | |
| 57 | Eric Richards | 197 | 2028-2044 | |
| 58 | Travis Barrett# | 196 | 2051-2064 | |
| 59 | Kelly Hoskinson | 195 | 2031-2046 | |
| 60 | Brody McIlmoyle | 193 | 2020-2035 | |
| 60 | Boddie Montgomery# | 193 | 2052-2065 | |
| 62 | Mohammed Alvarez | 192 | 2029-2044 | |
| 63 | Dax Ballard# | 189 | 2049-2064 | |
| 63 | Kelly Martin | 189 | 2031-2049 | |
| 63 | Grant Vickers | 189 | 2033-2046 | |
| 66 | Marian Chandler# | 188 | 2050-2065 | |
| 67 | Gary Richards | 187 | 2036-2053 | |
| 67 | Brian Woods | 187 | 2020-2033 | |
| 69 | Michael Bates | 186 | 2039-2055 | |
| 70 | Jason Floyd | 185 | 2041-2058 | |
| 70 | George Martos | 185 | 2047-2062 | |
| 72 | Rodrigo Navarro | 184 | 2035-2049 | |
| 72 | Bill O'Toole | 184 | 2050-2063 | |
| 74 | Mark Brantley# | 182 | 2052-2064 | |
| 74 | David Gangle | 182 | 2045-2059 | |
| 76 | Trevor Brooks | 181 | 2019-2032 | |
| 77 | Shane Hollingsworth | 180 | 2019-2035 | |
| 78 | Felix Romero | 179 | 2028-2045 | |
| 79 | Antonio Soto | 178 | 2020-2033 | |
| 79 | Matthew Weber# | 178 | 2050-2065 | |
| 81 | Raynald Charron | 176 | 2020-2037 | |
| 81 | Ricky Stanley | 176 | 2041-2054 | |
| 83 | Craig Byrd* | 175 | 2019-2028 | |
| 83 | Luis Rodriguez | 175 | 2033-2049 | |
| 83 | Rick Summers | 175 | 2035-2050 | |
| 86 | Tommy Murphy | 173 | 2035-2048 | |
| 87 | David Perez | 172 | 2038-2053 | |
| 88 | David Foster | 171 | 2045-2061 | |
| 88 | Jett Helms# | 171 | 2054-2065 | |
| 90 | Steven Lee | 170 | 2028-2043 | |
| 91 | Durante Montero | 169 | 2028-2039 | |
| 91 | Landon Ward# | 169 | 2054-2065 | |
| 93 | George Beckett | 168 | 2035-2050 | |
| 93 | Jesus Castillo | 168 | 2046-2061 | |
| 93 | Albert McQuillen | 168 | 2046-2060 | |
| 93 | Broderick Stewart | 168 | 2023-2038 | |
| 93 | David Vaughn | 168 | 2040-2059 | |
| 98 | Grant Cody | 167 | 2027-2041 | |
| 98 | Jimmy Hayes | 167 | 2035-2052 | |
| 98 | Scott Lachanski | 167 | 2032-2046 |
