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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 | Ryan Lee | 152 | 2067-2080 | |
| 10 | Aiden MacDougall | 152 | 2036-2050 | |
| 14 | Ryan Rose* | 150 | 2031-2042 | |
| 14 | Steven Slothsburg | 150 | 2061-2074 | |
| 16 | Andy Beans | 149 | 2065-2080 | |
| 16 | Xavier Crawford | 149 | 2053-2066 | |
| 18 | Blu Line* | 148 | 2027-2040 | |
| 18 | Glenallen Mixon* | 148 | 2043-2055 | |
| 20 | Regnaleb Sivart | 147 | 2032-2045 | |
| 21 | Athena Aria* | 145 | 2045-2058 | |
| 21 | Ryan Stryker Jr.* | 145 | 2055-2069 | |
| 23 | Chaz LaLocke | 143 | 2017-2030 | |
| 23 | Shoto Todoroki* | 143 | 2044-2056 | |
| 25 | Wright Indadert* | 142 | 2051-2062 | |
| 25 | Johnny Patey V2* | 142 | 2056-2068 | |
| 25 | PDub Woods | 142 | 2065-2078 | |
| 28 | John Cowgill# | 141 | 2068-2081 | |
| 28 | Pax Torrent* | 141 | 2050-2063 | |
| 30 | Taylor Adkins# | 139 | 2069-2081 | |
| 30 | Kevin Choate* | 139 | 2032-2044 | |
| 30 | Glyn Davies* | 139 | 2044-2057 | |
| 30 | Psy Duck* | 139 | 2054-2066 | |
| 30 | Man O'Rite | 139 | 2052-2067 | |
| 35 | Pax Abadeer* | 138 | 2042-2055 | |
| 35 | Booze Gooser* | 138 | 2045-2054 | |
| 35 | Giovani Sánchez* | 138 | 2042-2055 | |
| 38 | Bobby Daring* | 137 | 2034-2044 | |
| 38 | Giuseppe Jones* | 137 | 2048-2061 | |
| 38 | Guy Roussy | 137 | 2067-2079 | |
| 41 | Acheoar Hippocrites* | 136 | 2053-2067 | |
| 41 | S'Vanaleigh Mykutowicz* | 136 | 2047-2058 | |
| 43 | Starscream* | 135 | 2053-2064 | |
| 44 | Ivy de Vries# | 134 | 2067-2081 | |
| 44 | Chuck Nasty# | 134 | 2069-2081 | |
| 46 | Calm Chicken | 133 | 2067-2080 | |
| 46 | Oerjan Thrastarsen* | 133 | 2055-2067 | |
| 48 | Barack Obama* | 132 | 2030-2040 | |
| 48 | Harry Styles* | 132 | 2028-2039 | |
| 50 | Virzeiros Balqen | 131 | 2030-2045 | |
| 50 | Maurice Bernard | 131 | 2066-2079 | |
| 50 | Hugh Mann | 131 | 2052-2065 | |
| 53 | Johnny Tatum | 130 | 2065-2078 | |
| 54 | Always A. Bummus | 129 | 2066-2078 | |
| 54 | Joey Slothface | 129 | 2028-2041 | |
| 56 | Justin Ripsbahd* | 128 | 2032-2045 | |
| 56 | Jonny Tsunami II | 128 | 2052-2065 | |
| 58 | Mookie Banks* | 127 | 2020-2032 | |
| 58 | Dogwood Maple | 127 | 2039-2053 | |
| 58 | Ryan Stryker* | 127 | 2021-2035 | |
| 61 | Aria Bluesky | 126 | 2069-2080 | |
| 61 | Mac John# | 126 | 2069-2081 | |
| 61 | Remy Lebeau | 126 | 2068-2080 | |
| 61 | Sportsboy57 | 126 | 2045-2059 | |
| 65 | Penny Kowers* | 125 | 2017-2034 | |
| 65 | Phillip Thompson* | 125 | 2018-2028 | |
| 67 | James Daly | 124 | 2056-2068 | |
| 67 | Brian Eshleman Jr. | 124 | 2060-2072 | |
| 67 | Wombat Jones | 124 | 2063-2076 | |
| 70 | Frederick Birdington | 123 | 2025-2037 | |
| 70 | Khamati Kahn | 123 | 2018-2029 | |
| 72 | John Camden Jr | 122 | 2049-2059 | |
| 72 | Meo Hooper | 122 | 2051-2063 | |
| 72 | Hiro Nakamura | 122 | 2036-2048 | |
| 75 | Evil Dictator | 121 | 2047-2059 | |
| 75 | Wutcanisae Eksepurwelkam* | 121 | 2054-2065 | |
| 75 | Colby Koffman | 121 | 2066-2077 | |
| 75 | Justin Simms | 121 | 2038-2049 | |
| 79 | Rhydon Dirty* | 120 | 2043-2056 | |
| 79 | Herbie Farnworth | 120 | 2039-2052 | |
| 79 | Hunter Havok | 120 | 2043-2052 | |
| 79 | Brent Lomew* | 120 | 2029-2041 | |
| 79 | Remy Ratatouille | 120 | 2039-2050 | |
| 84 | Phil Donoghue | 119 | 2054-2066 | |
| 84 | Walrus Jones | 119 | 2048-2060 | |
| 84 | Quentin O'Quarters | 119 | 2049-2064 | |
| 84 | J.C. Swishman | 119 | 2065-2079 | |
| 88 | CC Bouchard | 118 | 2049-2062 | |
| 88 | Lizzie Mitchell | 118 | 2046-2061 | |
| 88 | Poe Scott* | 118 | 2045-2060 | |
| 88 | Dizzy Stoner | 118 | 2061-2072 | |
| 92 | Delly d'Dendecks | 117 | 2048-2062 | |
| 92 | Damian Jansen-Crenshaw | 117 | 2045-2056 | |
| 92 | Jonny Quest* | 117 | 2052-2064 | |
| 95 | Bazooka Joe | 116 | 2051-2062 | |
| 95 | Pedro Martini# | 116 | 2068-2081 | |
| 95 | Wendy Marvell* | 116 | 2047-2061 | |
| 95 | Molly Mitchell | 116 | 2036-2048 | |
| 99 | Artemis Aria | 115 | 2061-2072 | |
| 99 | Calloway Flowers | 115 | 2031-2042 |
