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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Greg Steiner* | 179 | 2018-2031 | |
| 2 | Victoria Secret* | 174 | 2017-2028 | |
| 3 | Guy Walker* | 170 | 2021-2034 | |
| 4 | Esteban Rodriguez* | 165 | 2017-2029 | |
| 5 | Elston Sinclair* | 156 | 2017-2029 | |
| 6 | Straightgas Homie* | 154 | 2042-2055 | |
| 7 | Walker Cato | 153 | 2034-2047 | |
| 8 | Ed Barker* | 152 | 2027-2039 | |
| 8 | J.A. Jabs* | 152 | 2026-2039 | |
| 8 | Aiden MacDougall | 152 | 2036-2050 | |
| 11 | Ryan Rose* | 150 | 2031-2042 | |
| 12 | Blu Line* | 148 | 2027-2040 | |
| 12 | Glenallen Mixon* | 148 | 2043-2055 | |
| 14 | Regnaleb Sivart | 147 | 2032-2045 | |
| 15 | Athena Aria* | 145 | 2045-2058 | |
| 16 | Chaz LaLocke | 143 | 2017-2030 | |
| 16 | Shoto Todoroki* | 143 | 2044-2056 | |
| 18 | Wright Indadert# | 142 | 2051-2062 | |
| 18 | Allegra McArena# | 142 | 2052-2062 | |
| 20 | Kevin Choate* | 139 | 2032-2044 | |
| 20 | Glyn Davies* | 139 | 2044-2057 | |
| 22 | Pax Abadeer | 138 | 2042-2055 | |
| 22 | Booze Gooser* | 138 | 2045-2054 | |
| 22 | Giovani Sánchez* | 138 | 2042-2055 | |
| 22 | Pax Torrent# | 138 | 2050-2062 | |
| 26 | Bobby Daring* | 137 | 2034-2044 | |
| 26 | Giuseppe Jones | 137 | 2048-2061 | |
| 28 | S'Vanaleigh Mykutowicz* | 136 | 2047-2058 | |
| 29 | Barack Obama* | 132 | 2030-2040 | |
| 29 | Harry Styles* | 132 | 2028-2039 | |
| 31 | Virzeiros Balqen | 131 | 2030-2045 | |
| 32 | Joey Slothface | 129 | 2028-2041 | |
| 33 | Justin Ripsbahd* | 128 | 2032-2045 | |
| 34 | Mookie Banks* | 127 | 2020-2032 | |
| 34 | Dogwood Maple | 127 | 2039-2053 | |
| 34 | Ryan Stryker* | 127 | 2021-2035 | |
| 37 | Sportsboy57 | 126 | 2045-2059 | |
| 38 | Penny Kowers* | 125 | 2017-2034 | |
| 38 | Phillip Thompson* | 125 | 2018-2028 | |
| 40 | Frederick Birdington | 123 | 2025-2037 | |
| 40 | Khamati Kahn | 123 | 2018-2029 | |
| 42 | John Camden Jr# | 122 | 2049-2059 | |
| 42 | Hiro Nakamura | 122 | 2036-2048 | |
| 44 | Evil Dictator | 121 | 2047-2059 | |
| 44 | Justin Simms | 121 | 2038-2049 | |
| 46 | Rhydon Dirty* | 120 | 2043-2056 | |
| 46 | Herbie Farnworth | 120 | 2039-2052 | |
| 46 | Hunter Havok | 120 | 2043-2052 | |
| 46 | Brent Lomew* | 120 | 2029-2041 | |
| 46 | Man O'Rite# | 120 | 2052-2062 | |
| 46 | Remy Ratatouille | 120 | 2039-2050 | |
| 52 | Walrus Jones | 119 | 2048-2060 | |
| 53 | CC Bouchard# | 118 | 2049-2062 | |
| 53 | Lizzie Mitchell | 118 | 2046-2061 | |
| 53 | Poe Scott | 118 | 2045-2060 | |
| 56 | Delly d'Dendecks# | 117 | 2048-2062 | |
| 56 | Damian Jansen-Crenshaw | 117 | 2045-2056 | |
| 58 | Meo Hooper# | 116 | 2051-2062 | |
| 58 | Bazooka Joe# | 116 | 2051-2062 | |
| 58 | Wendy Marvell | 116 | 2047-2061 | |
| 58 | Molly Mitchell | 116 | 2036-2048 | |
| 62 | Calloway Flowers | 115 | 2031-2042 | |
| 62 | Buster Nutt* | 115 | 2029-2040 | |
| 62 | Stryker Spinrate | 115 | 2031-2042 | |
| 62 | Vivi Zielman* | 115 | 2036-2046 | |
| 66 | Billy Grier | 114 | 2038-2049 | |
| 66 | Taylor Johnson | 114 | 2034-2044 | |
| 68 | Xavier Crawford# | 113 | 2053-2062 | |
| 68 | Quentin O'Quarters# | 113 | 2049-2062 | |
| 70 | Peter Dawson | 112 | 2026-2036 | |
| 70 | Andrew Lucas* | 112 | 2036-2046 | |
| 70 | Hayley MaConnell* | 112 | 2026-2037 | |
| 73 | Sam Antonio | 111 | 2048-2062 | |
| 73 | Cesar Azuaje# | 111 | 2050-2062 | |
| 73 | Jonny Tsunami II# | 111 | 2052-2062 | |
| 76 | Michael Dion | 110 | 2039-2049 | |
| 76 | Lucky El Charro* | 110 | 2037-2049 | |
| 76 | PM Schramm | 110 | 2045-2061 | |
| 79 | Jose Forty-Three* | 109 | 2031-2043 | |
| 79 | Starscream# | 109 | 2053-2062 | |
| 79 | Eijun Wozy | 109 | 2017-2026 | |
| 82 | D'Aroldis Borkman* | 108 | 2018-2031 | |
| 82 | Nate Pearson* | 108 | 2029-2039 | |
| 82 | Tom Riddle | 108 | 2042-2055 | |
| 85 | Bark Muehrle* | 107 | 2041-2057 | |
| 85 | Tyler Oles | 107 | 2021-2033 | |
| 85 | Danny Sullivan | 107 | 2041-2051 | |
| 88 | Erick Bolanos | 105 | 2039-2049 | |
| 88 | "Big Rig" Tig O'Sullivan | 105 | 2044-2056 | |
| 90 | Psy Duck# | 104 | 2054-2062 | |
| 90 | King George III | 104 | 2040-2049 | |
| 90 | Gionna Morgan | 104 | 2048-2060 | |
| 93 | Austin Bentley | 103 | 2031-2043 | |
| 93 | Parker Parton | 103 | 2045-2058 | |
| 93 | Rickie Vaughne | 103 | 2036-2047 | |
| 96 | Alexander Benjamin | 102 | 2047-2062 | |
| 96 | Barry B Benson | 102 | 2042-2051 | |
| 96 | Via Getty | 102 | 2036-2047 | |
| 96 | Anthony Parco | 102 | 2052-2061 | |
| 100 | Randy Koufax | 101 | 2017-2027 |
