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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Allegra McArena* | 188 | 2052-2067 | |
| 2 | Greg Steiner* | 179 | 2018-2031 | |
| 3 | Victoria Secret* | 174 | 2017-2028 | |
| 4 | Guy Walker* | 170 | 2021-2034 | |
| 5 | Esteban Rodriguez* | 165 | 2017-2029 | |
| 6 | Nova Montagne* | 156 | 2057-2069 | |
| 6 | Elston Sinclair* | 156 | 2017-2029 | |
| 8 | Straightgas Homie* | 154 | 2042-2055 | |
| 9 | Walker Cato | 153 | 2034-2047 | |
| 10 | Ed Barker* | 152 | 2027-2039 | |
| 10 | J.A. Jabs* | 152 | 2026-2039 | |
| 10 | Aiden MacDougall | 152 | 2036-2050 | |
| 13 | Ryan Rose* | 150 | 2031-2042 | |
| 13 | Steven Slothsburg | 150 | 2061-2074 | |
| 15 | Xavier Crawford | 149 | 2053-2066 | |
| 16 | Blu Line* | 148 | 2027-2040 | |
| 16 | Glenallen Mixon* | 148 | 2043-2055 | |
| 18 | Regnaleb Sivart | 147 | 2032-2045 | |
| 19 | Athena Aria* | 145 | 2045-2058 | |
| 19 | Ryan Stryker Jr.* | 145 | 2055-2069 | |
| 21 | Chaz LaLocke | 143 | 2017-2030 | |
| 21 | Shoto Todoroki* | 143 | 2044-2056 | |
| 23 | Wright Indadert* | 142 | 2051-2062 | |
| 23 | Johnny Patey V2 | 142 | 2056-2068 | |
| 25 | Pax Torrent* | 141 | 2050-2063 | |
| 26 | Kevin Choate* | 139 | 2032-2044 | |
| 26 | Glyn Davies* | 139 | 2044-2057 | |
| 26 | Psy Duck* | 139 | 2054-2066 | |
| 26 | Man O'Rite | 139 | 2052-2067 | |
| 30 | Pax Abadeer* | 138 | 2042-2055 | |
| 30 | Andy Beans# | 138 | 2065-2078 | |
| 30 | Booze Gooser* | 138 | 2045-2054 | |
| 30 | Giovani Sánchez* | 138 | 2042-2055 | |
| 34 | Bobby Daring* | 137 | 2034-2044 | |
| 34 | Giuseppe Jones* | 137 | 2048-2061 | |
| 34 | PDub Woods# | 137 | 2065-2078 | |
| 37 | Acheoar Hippocrites | 136 | 2053-2067 | |
| 37 | S'Vanaleigh Mykutowicz* | 136 | 2047-2058 | |
| 39 | Starscream* | 135 | 2053-2064 | |
| 40 | Oerjan Thrastarsen* | 133 | 2055-2067 | |
| 41 | Barack Obama* | 132 | 2030-2040 | |
| 41 | Harry Styles* | 132 | 2028-2039 | |
| 43 | Virzeiros Balqen | 131 | 2030-2045 | |
| 43 | Hugh Mann | 131 | 2052-2065 | |
| 45 | Joey Slothface | 129 | 2028-2041 | |
| 45 | Johnny Tatum# | 129 | 2065-2078 | |
| 47 | Always A. Bummus# | 128 | 2066-2078 | |
| 47 | Justin Ripsbahd* | 128 | 2032-2045 | |
| 47 | Jonny Tsunami II | 128 | 2052-2065 | |
| 50 | Mookie Banks* | 127 | 2020-2032 | |
| 50 | Dogwood Maple | 127 | 2039-2053 | |
| 50 | Ryan Stryker* | 127 | 2021-2035 | |
| 53 | Sportsboy57 | 126 | 2045-2059 | |
| 54 | Penny Kowers* | 125 | 2017-2034 | |
| 54 | Guy Roussy# | 125 | 2067-2078 | |
| 54 | Phillip Thompson* | 125 | 2018-2028 | |
| 57 | James Daly | 124 | 2056-2068 | |
| 57 | Brian Eshleman Jr. | 124 | 2060-2072 | |
| 57 | Wombat Jones | 124 | 2063-2076 | |
| 60 | Frederick Birdington | 123 | 2025-2037 | |
| 60 | Khamati Kahn | 123 | 2018-2029 | |
| 62 | John Camden Jr | 122 | 2049-2059 | |
| 62 | Meo Hooper | 122 | 2051-2063 | |
| 62 | Hiro Nakamura | 122 | 2036-2048 | |
| 65 | Evil Dictator | 121 | 2047-2059 | |
| 65 | Wutcanisae Eksepurwelkam* | 121 | 2054-2065 | |
| 65 | Colby Koffman | 121 | 2066-2077 | |
| 65 | Justin Simms | 121 | 2038-2049 | |
| 69 | Rhydon Dirty* | 120 | 2043-2056 | |
| 69 | Herbie Farnworth | 120 | 2039-2052 | |
| 69 | Hunter Havok | 120 | 2043-2052 | |
| 69 | Brent Lomew* | 120 | 2029-2041 | |
| 69 | Remy Ratatouille | 120 | 2039-2050 | |
| 74 | Phil Donoghue | 119 | 2054-2066 | |
| 74 | Walrus Jones | 119 | 2048-2060 | |
| 74 | Quentin O'Quarters | 119 | 2049-2064 | |
| 77 | CC Bouchard | 118 | 2049-2062 | |
| 77 | Ryan Lee# | 118 | 2067-2078 | |
| 77 | Lizzie Mitchell | 118 | 2046-2061 | |
| 77 | Poe Scott* | 118 | 2045-2060 | |
| 77 | Dizzy Stoner | 118 | 2061-2072 | |
| 82 | Maurice Bernard# | 117 | 2066-2078 | |
| 82 | Delly d'Dendecks | 117 | 2048-2062 | |
| 82 | Damian Jansen-Crenshaw | 117 | 2045-2056 | |
| 82 | Jonny Quest* | 117 | 2052-2064 | |
| 86 | Bazooka Joe | 116 | 2051-2062 | |
| 86 | Wendy Marvell* | 116 | 2047-2061 | |
| 86 | Molly Mitchell | 116 | 2036-2048 | |
| 89 | Artemis Aria | 115 | 2061-2072 | |
| 89 | Calloway Flowers | 115 | 2031-2042 | |
| 89 | Joey Moose Jr. | 115 | 2066-2077 | |
| 89 | Buster Nutt* | 115 | 2029-2040 | |
| 89 | Shohei Ohtani | 115 | 2057-2073 | |
| 89 | Stryker Spinrate | 115 | 2031-2042 | |
| 89 | Vivi Zielman* | 115 | 2036-2046 | |
| 96 | Ivy de Vries# | 114 | 2067-2078 | |
| 96 | Center Fielder | 114 | 2060-2073 | |
| 96 | Kelvin Gauzeman | 114 | 2058-2070 | |
| 96 | Billy Grier | 114 | 2038-2049 | |
| 96 | Taylor Johnson | 114 | 2034-2044 |
