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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Garrett Corthright | 18 | 2014-2017 | |
| 1 | Steven Gallardo | 18 | 2013-2021 | |
| 1 | Niall Windeler# | 18 | 2020-2025 | |
| 4 | Elias Pinales | 17 | 2013-2019 | |
| 4 | Jake Webb# | 17 | 2018-2025 | |
| 6 | Nic Hanson | 15 | 2013-2023 | |
| 7 | David Hurlbut | 14 | 2013-2019 | |
| 7 | Eric Pardinho# | 14 | 2020-2025 | |
| 7 | Tayler Scott# | 14 | 2013-2015 | |
| 7 | Sean Sullivan# | 14 | 2022-2025 | |
| 11 | Brennan Bernardino# | 13 | 2016-2017 | |
| 11 | Joseph Krehbiel# | 13 | 2013-2015 | |
| 11 | Ryan Newell | 13 | 2013-2017 | |
| 11 | Radhames Quezada | 13 | 2013-2016 | |
| 11 | Max Roberts# | 13 | 2018-2021 | |
| 11 | Zach Wolf# | 13 | 2020-2025 | |
| 17 | Edwin Diaz# | 12 | 2013-2015 | |
| 17 | Chris Flexen# | 12 | 2013-2015 | |
| 17 | Zachary Leigh# | 12 | 2022-2025 | |
| 17 | Kieran Lovegrove | 12 | 2014-2017 | |
| 17 | Daiveyon Whittle# | 12 | 2019-2025 | |
| 22 | Zachary Bird | 11 | 2013-2023 | |
| 22 | Mitch Horacek | 11 | 2014-2016 | |
| 22 | Chih-Wei Hu | 11 | 2014-2015 | |
| 22 | Keenan Kish | 11 | 2016-2017 | |
| 22 | Cody Kurz | 11 | 2013-2016 | |
| 22 | Nick Lee | 11 | 2013-2016 | |
| 22 | M.T. Minacci | 11 | 2016-2018 | |
| 22 | Mark Mixon | 11 | 2020-2023 | |
| 22 | Javier Reynoso | 11 | 2017-2022 | |
| 22 | Orlando Ribalta# | 11 | 2020-2024 | |
| 22 | Erian Rodriguez# | 11 | 2022-2025 | |
| 22 | Chris Vallimont# | 11 | 2019-2020 | |
| 34 | Luarbert Arias# | 10 | 2022-2025 | |
| 34 | Matt Ball | 10 | 2014-2017 | |
| 34 | Mike Clevinger# | 10 | 2013-2014 | |
| 34 | Colton Cross | 10 | 2016-2018 | |
| 34 | Ethan Hammerberg# | 10 | 2024-2025 | |
| 34 | Adrian Houser# | 10 | 2013-2016 | |
| 34 | Ryne Inman | 10 | 2017-2021 | |
| 34 | Pat Light | 10 | 2013-2015 | |
| 34 | Nate Savino# | 10 | 2023-2025 | |
| 34 | Jake Stevenson | 10 | 2020-2022 | |
| 44 | Diomenges Almengo# | 9 | 2016-2025 | |
| 44 | Jhosmer Alvarez# | 9 | 2024-2025 | |
| 44 | Pat Connaughton | 9 | 2015-2019 | |
| 44 | Scott DeCecco | 9 | 2013-2015 | |
| 44 | Jeremiah Estrada# | 9 | 2019-2021 | |
| 44 | Bailey Falter# | 9 | 2016-2018 | |
| 44 | Jacob Forrester | 9 | 2020-2023 | |
| 44 | Tyler Garbee# | 9 | 2020-2022 | |
| 44 | Luke Gillingham | 9 | 2018-2018 | |
| 44 | Tyler Gough# | 9 | 2023-2025 | |
| 44 | Scott Grist | 9 | 2016-2019 | |
| 44 | Stepan Havlicek | 9 | 2013-2022 | |
| 44 | Nicholas Johnson# | 9 | 2019-2024 | |
| 44 | Zachary Jones | 9 | 2013-2015 | |
| 44 | David Lucroy | 9 | 2016-2017 | |
| 44 | Mitch McKown | 9 | 2019-2023 | |
| 44 | Craig Missigman | 9 | 2014-2017 | |
| 44 | Frank Mozzicato# | 9 | 2022-2025 | |
| 44 | Alexander Muren | 9 | 2013-2015 | |
| 44 | Daniel Nunan# | 9 | 2020-2022 | |
| 44 | Zach Quintana | 9 | 2013-2016 | |
| 44 | Grayson Rodriguez# | 9 | 2019-2023 | |
| 44 | Brady Schanuel# | 9 | 2020-2025 | |
| 44 | Johnnie Schneider | 9 | 2020-2022 | |
| 44 | David Sosebee | 9 | 2016-2022 | |
| 44 | Matthew Swain# | 9 | 2020-2025 | |
| 44 | Carlos Torres# | 9 | 2023-2024 | |
| 44 | Kyle Twomey | 9 | 2016-2017 | |
| 44 | Zakery Wasilewski | 9 | 2013-2016 | |
| 73 | Casey Anderson# | 8 | 2024-2025 | |
| 73 | Jacob Blank | 8 | 2019-2021 | |
| 73 | Logan Boyd | 8 | 2016-2017 | |
| 73 | Garrison Bryant | 8 | 2018-2020 | |
| 73 | Brock Burke# | 8 | 2015-2018 | |
| 73 | Chandler Champlain# | 8 | 2022-2025 | |
| 73 | Zachary Correll | 8 | 2016-2016 | |
| 73 | Kevin Coulter | 8 | 2020-2021 | |
| 73 | Derek De Young | 8 | 2013-2015 | |
| 73 | Brock Dykxhoorn | 8 | 2017-2020 | |
| 73 | Scott Effross# | 8 | 2016-2018 | |
| 73 | Evan Estes | 8 | 2019-2021 | |
| 73 | Andrew Ferreira | 8 | 2013-2015 | |
| 73 | Conor Fisk | 8 | 2016-2017 | |
| 73 | A.J. Franklin | 8 | 2020-2020 | |
| 73 | Kody Funderburk# | 8 | 2019-2019 | |
| 73 | Lucas Giolito# | 8 | 2013-2015 | |
| 73 | Scott Griggs | 8 | 2013-2016 | |
| 73 | Anthony Guardado | 8 | 2016-2018 | |
| 73 | Bradley Hanner# | 8 | 2020-2022 | |
| 73 | Thatcher Hurd# | 8 | 2025-2025 | |
| 73 | Kyle Jones# | 8 | 2023-2025 | |
| 73 | Francisco Martinez# | 8 | 2021-2025 | |
| 73 | Pearson McMahan# | 8 | 2018-2022 | |
| 73 | Juan Meza | 8 | 2016-2022 | |
| 73 | Kyle Miller | 8 | 2016-2017 | |
| 73 | Mark Moclair# | 8 | 2021-2025 | |
| 73 | Alexander Montero# | 8 | 2021-2025 |
