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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Alec Kisena | 4 | 2022-2024 | |
| 1 | Zach McCambley# | 4 | 2022-2024 | |
| 1 | Jason Stoffel | 4 | 2013-2017 | |
| 1 | Danny Young# | 4 | 2018-2024 | |
| 5 | Christian Binford | 3 | 2015-2016 | |
| 5 | Greg Nappo | 3 | 2016-2018 | |
| 5 | Martin Perez# | 3 | 2013-2019 | |
| 5 | Scott Williams | 3 | 2018-2021 | |
| 9 | Spencer Adams | 2 | 2017-2019 | |
| 9 | Tyler Chatwood | 2 | 2013-2013 | |
| 9 | Brody Colvin | 2 | 2013-2016 | |
| 9 | Matt Gage# | 2 | 2017-2024 | |
| 9 | Kyle Hart# | 2 | 2019-2023 | |
| 9 | Taylor Hearn# | 2 | 2020-2021 | |
| 9 | Eric Jokisch# | 2 | 2014-2018 | |
| 9 | Connor Loeprich# | 2 | 2023-2024 | |
| 9 | Zachary Lovvorn | 2 | 2019-2021 | |
| 9 | Julian Merryweather# | 2 | 2017-2020 | |
| 9 | Franklin Morales | 2 | 2014-2015 | |
| 9 | Adam Morgan | 2 | 2013-2023 | |
| 9 | Zach Petrick | 2 | 2014-2016 | |
| 9 | Alan Rangel# | 2 | 2022-2025 | |
| 9 | David Speer | 2 | 2019-2021 | |
| 9 | Louie Varland# | 2 | 2022-2023 | |
| 9 | Zack Wheeler# | 2 | 2013-2013 | |
| 26 | Andrew Albers | 1 | 2013-2015 | |
| 26 | Matt Andriese | 1 | 2014-2016 | |
| 26 | Shawn Armstrong# | 1 | 2014-2015 | |
| 26 | D.J. Baxendale | 1 | 2019-2019 | |
| 26 | Aaron Blair | 1 | 2016-2020 | |
| 26 | Denny Brady# | 1 | 2020-2021 | |
| 26 | Marc Brakeman | 1 | 2018-2021 | |
| 26 | Colten Brewer# | 1 | 2021-2024 | |
| 26 | Dan Camarena# | 1 | 2022-2022 | |
| 26 | Trevor Clifton# | 1 | 2020-2024 | |
| 26 | Tim Crabbe | 1 | 2015-2016 | |
| 26 | Malcolm Culver | 1 | 2016-2017 | |
| 26 | Garrett Davila# | 1 | 2022-2025 | |
| 26 | Jose De Paula | 1 | 2013-2014 | |
| 26 | Josh Degraaf | 1 | 2019-2021 | |
| 26 | Ross Detwiler | 1 | 2016-2019 | |
| 26 | Bobby Doran | 1 | 2013-2016 | |
| 26 | Kyle Drabek | 1 | 2017-2017 | |
| 26 | Jon Edwards | 1 | 2015-2021 | |
| 26 | Luke Eubank | 1 | 2019-2021 | |
| 26 | Nelson Gonzalez | 1 | 2018-2019 | |
| 26 | Ashton Goudeau | 1 | 2017-2022 | |
| 26 | Reymin Guduan | 1 | 2019-2019 | |
| 26 | Angel Heredia | 1 | 2018-2019 | |
| 26 | Matt Hoffman | 1 | 2013-2015 | |
| 26 | J.J. Hoover | 1 | 2017-2019 | |
| 26 | Colt Hynes | 1 | 2014-2018 | |
| 26 | William Kelly | 1 | 2017-2017 | |
| 26 | Dean Kiekhefer | 1 | 2014-2016 | |
| 26 | Mark Lamm | 1 | 2014-2016 | |
| 26 | Joel Linares | 1 | 2016-2016 | |
| 26 | Grayson Long | 1 | 2017-2019 | |
| 26 | Daniel Lynch# | 1 | 2020-2021 | |
| 26 | Joe Mantiply# | 1 | 2021-2021 | |
| 26 | Griff McGarry# | 1 | 2023-2024 | |
| 26 | Yoel Mecias | 1 | 2017-2018 | |
| 26 | Sean Mooney# | 1 | 2022-2025 | |
| 26 | A.J. Morris | 1 | 2013-2017 | |
| 26 | Reese Olson# | 1 | 2022-2023 | |
| 26 | Andy Otero | 1 | 2022-2022 | |
| 26 | Carson Palmquist# | 1 | 2024-2024 | |
| 26 | Ivan Pineyro | 1 | 2017-2017 | |
| 26 | Cal Quantrill# | 1 | 2019-2021 | |
| 26 | Andrew Quezada# | 1 | 2022-2024 | |
| 26 | Neil Ramirez | 1 | 2019-2019 | |
| 26 | Chris Reed | 1 | 2013-2021 | |
| 26 | Manuel Rodriguez# | 1 | 2022-2024 | |
| 26 | Enny Romero | 1 | 2019-2020 | |
| 26 | Joe Ross# | 1 | 2015-2015 | |
| 26 | Ramon Rosso# | 1 | 2020-2024 | |
| 26 | Frank Rubio | 1 | 2020-2021 | |
| 26 | Josh Sborz# | 1 | 2017-2023 | |
| 26 | Andrew Schultz# | 1 | 2020-2020 | |
| 26 | Davis Sharpe# | 1 | 2024-2024 | |
| 26 | Daniel Slania | 1 | 2017-2021 | |
| 26 | Drew Smith# | 1 | 2018-2025 | |
| 26 | Cole Sulser# | 1 | 2017-2019 | |
| 26 | Peter Tago | 1 | 2022-2022 | |
| 26 | Freddy Tarnok# | 1 | 2024-2025 | |
| 26 | Jackson Tetreault# | 1 | 2019-2024 | |
| 26 | Kanekoa Texeira | 1 | 2013-2016 | |
| 26 | Reagan Todd# | 1 | 2024-2024 | |
| 26 | Loek Van Mil | 1 | 2013-2017 | |
| 26 | Pat Venditte | 1 | 2019-2021 | |
| 26 | Tyler Viza# | 1 | 2019-2019 | |
| 26 | Matt Vogel# | 1 | 2021-2024 | |
| 26 | Jeremy Walker | 1 | 2018-2020 | |
| 26 | Josh Wall | 1 | 2013-2015 | |
| 26 | Brandon Walter# | 1 | 2022-2024 | |
| 26 | Ryan Weathers# | 1 | 2022-2024 | |
| 26 | Ryan Williams | 1 | 2017-2019 | |
| 26 | Ben Yokley | 1 | 2016-2016 | |
| 98 | Kenedy Agramonte | 0 | 2015-2017 | |
| 98 | Raul Alcantara# | 0 | 2018-2021 | |
| 98 | Elvis Araujo | 0 | 2021-2021 |
