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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Christian Bergman | 43 | 2014-2019 | |
| 2 | Deck McGuire | 40 | 2014-2019 | |
| 3 | Conner Menez# | 35 | 2019-2023 | |
| 4 | Sam Howard# | 34 | 2017-2023 | |
| 4 | Jason Hursh | 34 | 2014-2020 | |
| 6 | Casey Coleman# | 33 | 2013-2023 | |
| 6 | Blake Treinen# | 33 | 2014-2016 | |
| 8 | Carlos Contreras | 32 | 2014-2017 | |
| 9 | Arnaldo Hernandez# | 31 | 2016-2021 | |
| 9 | Taylor Hill | 31 | 2014-2018 | |
| 9 | Steven Johnson | 31 | 2013-2017 | |
| 12 | Matt Dermody# | 30 | 2017-2023 | |
| 13 | Kyle T. Smith# | 29 | 2016-2023 | |
| 14 | Austin Bibens-Dirkx | 28 | 2014-2018 | |
| 14 | Danny Rosenbaum | 28 | 2013-2015 | |
| 16 | Severino Gonzalez | 27 | 2014-2019 | |
| 17 | Jason Garcia# | 26 | 2015-2020 | |
| 17 | Sean Nolin | 26 | 2013-2015 | |
| 19 | Trevor Bauer# | 25 | 2013-2014 | |
| 19 | Thomas Eshelman# | 25 | 2016-2023 | |
| 19 | Jordan Stephens# | 25 | 2019-2023 | |
| 22 | Sam Perez# | 24 | 2018-2023 | |
| 23 | Chris Gloor | 23 | 2013-2016 | |
| 23 | Carlos Pimentel | 23 | 2014-2017 | |
| 23 | Henry Sosa | 23 | 2013-2016 | |
| 23 | Jordan Yamamoto# | 23 | 2016-2023 | |
| 27 | Garrett Cleavinger# | 22 | 2017-2022 | |
| 27 | Tommy Milone# | 22 | 2018-2020 | |
| 27 | Thomas Szapucki# | 22 | 2018-2022 | |
| 27 | Matthew Tomshaw | 22 | 2016-2021 | |
| 27 | Matthew Tracy | 22 | 2016-2019 | |
| 27 | Marcus Walden | 22 | 2014-2022 | |
| 33 | Simon Castro | 21 | 2013-2016 | |
| 33 | Alec Marsh# | 21 | 2022-2023 | |
| 33 | Hector Perez# | 21 | 2019-2023 | |
| 33 | Andrew Wantz# | 21 | 2020-2021 | |
| 37 | Matt Barnes# | 20 | 2013-2014 | |
| 37 | Jon Heasley# | 20 | 2022-2023 | |
| 37 | Yohander Mendez# | 20 | 2015-2021 | |
| 37 | Matt Pierpont | 20 | 2017-2021 | |
| 37 | Aaron West | 20 | 2013-2017 | |
| 42 | Jason Adam# | 19 | 2015-2022 | |
| 42 | Jacob Bray | 19 | 2019-2022 | |
| 42 | Genesis Cabrera# | 19 | 2019-2021 | |
| 42 | Adrian De Horta# | 19 | 2019-2023 | |
| 42 | Brady Feigl# | 19 | 2019-2023 | |
| 42 | Kevin Herget# | 19 | 2017-2021 | |
| 42 | Gregory Infante | 19 | 2013-2017 | |
| 42 | Jake Kalish# | 19 | 2018-2020 | |
| 42 | Kyle Kubat# | 19 | 2019-2023 | |
| 42 | Kyle Lobstein | 19 | 2017-2020 | |
| 42 | Kevin McCarthy | 19 | 2015-2022 | |
| 42 | Keury Mella# | 19 | 2018-2023 | |
| 42 | Cody Reed# | 19 | 2017-2020 | |
| 42 | William Roberts | 19 | 2015-2017 | |
| 42 | Forrest Snow | 19 | 2015-2019 | |
| 57 | Sam Coonrod# | 18 | 2017-2023 | |
| 57 | Nick Fanti# | 18 | 2016-2021 | |
| 57 | Andrew Faulkner# | 18 | 2014-2021 | |
| 57 | Percy Garner | 18 | 2014-2016 | |
| 57 | Anthony Kay# | 18 | 2019-2023 | |
| 57 | Phillipp Klein | 18 | 2014-2017 | |
| 57 | Ian McKinney# | 18 | 2018-2023 | |
| 57 | Jameson Taillon# | 18 | 2013-2014 | |
| 57 | Colton Turner | 18 | 2017-2021 | |
| 57 | Tyler Watson# | 18 | 2021-2023 | |
| 57 | Steven Wright | 18 | 2013-2021 | |
| 68 | Dustin Beggs# | 17 | 2019-2021 | |
| 68 | Matthew Bowman# | 17 | 2014-2021 | |
| 68 | Aaron Brooks | 17 | 2016-2019 | |
| 68 | Jake Faria# | 17 | 2016-2023 | |
| 68 | Bowden Francis# | 17 | 2020-2022 | |
| 68 | Alec Hansen | 17 | 2019-2021 | |
| 68 | Andrew Istler# | 17 | 2019-2023 | |
| 68 | Walker Lockett# | 17 | 2017-2020 | |
| 68 | Cole Sands# | 17 | 2022-2023 | |
| 68 | Jesse Scholtens# | 17 | 2020-2021 | |
| 68 | Greg Smith | 17 | 2013-2016 | |
| 68 | Jacob Turner | 17 | 2017-2020 | |
| 68 | Adam Wilk | 17 | 2013-2019 | |
| 68 | Tommy Wilson# | 17 | 2021-2023 | |
| 82 | Ruben Alaniz# | 16 | 2014-2022 | |
| 82 | Nabil Crismatt# | 16 | 2017-2018 | |
| 82 | Miguel Del Pozo# | 16 | 2019-2023 | |
| 82 | Edwin Fierro | 16 | 2018-2022 | |
| 82 | Jon Harris# | 16 | 2018-2023 | |
| 82 | Gage Hinsz# | 16 | 2018-2023 | |
| 82 | Tyson Miller# | 16 | 2020-2022 | |
| 82 | Brian Moran# | 16 | 2013-2023 | |
| 82 | Chris O'Grady | 16 | 2017-2020 | |
| 82 | Sean O'Sullivan | 16 | 2014-2018 | |
| 82 | Andy Oliver | 16 | 2013-2018 | |
| 82 | A.J. Puckett# | 16 | 2017-2023 | |
| 82 | Tom Robson | 16 | 2014-2020 | |
| 82 | Mark Sappington | 16 | 2015-2017 | |
| 82 | Misael Siverio | 16 | 2016-2018 | |
| 82 | Cy Sneed# | 16 | 2017-2019 | |
| 82 | Josh Taylor# | 16 | 2017-2022 | |
| 99 | Logan Allen# | 15 | 2019-2020 | |
| 99 | Edgar Arredondo# | 15 | 2019-2023 |
