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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Noah Davis# | 19 | 2020-2022 | |
| 2 | Justin Jarvis# | 18 | 2019-2022 | |
| 2 | Yankory Pimentel | 18 | 2016-2018 | |
| 4 | Nick Lockhart# | 16 | 2021-2024 | |
| 5 | Travis Adams# | 15 | 2022-2024 | |
| 5 | Ryan Sherriff | 15 | 2013-2016 | |
| 5 | Ricky Vanasco# | 15 | 2018-2020 | |
| 8 | Tai Tiedemann | 14 | 2017-2022 | |
| 9 | Patrick Murphy# | 13 | 2014-2018 | |
| 10 | Julio Felix | 12 | 2013-2019 | |
| 10 | Seth Johnson# | 12 | 2020-2021 | |
| 10 | John King# | 12 | 2019-2020 | |
| 10 | Junior Mendez | 12 | 2014-2016 | |
| 10 | Jose Mesa Jr. | 12 | 2013-2017 | |
| 10 | Jeff Soptic | 12 | 2013-2016 | |
| 16 | Joe Barlow# | 11 | 2017-2018 | |
| 16 | Ty Buttrey# | 11 | 2013-2015 | |
| 16 | Garrett Davila# | 11 | 2016-2018 | |
| 16 | Caleb Frare | 11 | 2013-2015 | |
| 16 | Mike Gomez | 11 | 2015-2016 | |
| 16 | Logan Longwith | 11 | 2016-2018 | |
| 16 | Angel Macuare# | 11 | 2020-2021 | |
| 16 | Damien Magnifico | 11 | 2014-2015 | |
| 16 | Bryan Martinez | 11 | 2021-2023 | |
| 16 | Geordy Parra | 11 | 2015-2017 | |
| 26 | Trevor Belicek | 10 | 2017-2018 | |
| 26 | Mitch Brown | 10 | 2013-2014 | |
| 26 | Andrew Dalquist# | 10 | 2020-2024 | |
| 26 | Edgar Gonzalez | 10 | 2022-2022 | |
| 26 | Erik Rivera# | 10 | 2021-2024 | |
| 26 | Sam Romero | 10 | 2020-2023 | |
| 26 | Corey Walter | 10 | 2015-2016 | |
| 26 | Jonah Wesely | 10 | 2014-2017 | |
| 26 | Cole Wiper | 10 | 2014-2016 | |
| 35 | Yhoan Acosta | 9 | 2016-2018 | |
| 35 | Aaron Bummer# | 9 | 2015-2017 | |
| 35 | Brad Case# | 9 | 2019-2020 | |
| 35 | Connor Coward | 9 | 2019-2019 | |
| 35 | Justin Crump# | 9 | 2020-2024 | |
| 35 | Scott Frazier | 9 | 2014-2017 | |
| 35 | Cody Hacker | 9 | 2020-2022 | |
| 35 | Stephen Jones# | 9 | 2021-2023 | |
| 35 | Danny Keller | 9 | 2013-2015 | |
| 35 | Austin Krob# | 9 | 2024-2024 | |
| 35 | Joseph Maher | 9 | 2013-2015 | |
| 35 | Gunner Mayer# | 9 | 2020-2024 | |
| 35 | Jaylen Nowlin# | 9 | 2022-2023 | |
| 35 | Pierson Ohl# | 9 | 2023-2023 | |
| 35 | Reese Olson# | 9 | 2020-2021 | |
| 35 | Julio Pinto | 9 | 2020-2023 | |
| 35 | Bodi Rascon# | 9 | 2022-2024 | |
| 35 | Luc Rennie | 9 | 2013-2015 | |
| 35 | Nash Walters# | 9 | 2017-2022 | |
| 35 | Trevor Williams# | 9 | 2014-2015 | |
| 35 | Tyler Willman | 9 | 2015-2020 | |
| 56 | Matt Brash# | 8 | 2020-2021 | |
| 56 | Hever Bueno | 8 | 2017-2020 | |
| 56 | A.J. Burke | 8 | 2014-2016 | |
| 56 | Hyun-il Choi# | 8 | 2022-2024 | |
| 56 | Jacob Constante | 8 | 2013-2017 | |
| 56 | Jefferson Figueroa# | 8 | 2021-2024 | |
| 56 | Michael Flynn# | 8 | 2019-2020 | |
| 56 | Dalton Friend | 8 | 2013-2015 | |
| 56 | Marc Iseneker | 8 | 2018-2018 | |
| 56 | Cory Jones | 8 | 2013-2015 | |
| 56 | Jacob Kostyshock# | 8 | 2020-2024 | |
| 56 | Juan Pablo Lopez# | 8 | 2022-2024 | |
| 56 | Quinton Low# | 8 | 2022-2024 | |
| 56 | Adam Maier# | 8 | 2023-2024 | |
| 56 | Michael Morales# | 8 | 2022-2024 | |
| 56 | Mike Morin | 8 | 2013-2014 | |
| 56 | Austin Nicely | 8 | 2015-2016 | |
| 56 | Conner Nurse# | 8 | 2019-2022 | |
| 56 | Steven Okert# | 8 | 2013-2014 | |
| 56 | Kaleb Ort# | 8 | 2019-2024 | |
| 56 | Wesley Scott# | 8 | 2023-2024 | |
| 56 | Jose Taveras | 8 | 2018-2023 | |
| 56 | Nick Thwaits# | 8 | 2020-2024 | |
| 56 | Jose Torres | 8 | 2015-2016 | |
| 56 | Jose Valdez | 8 | 2013-2014 | |
| 56 | Shane Watson | 8 | 2013-2014 | |
| 82 | Scott Barlow# | 7 | 2014-2016 | |
| 82 | Josh Burgmann# | 7 | 2020-2024 | |
| 82 | Tanner Bushue | 7 | 2013-2016 | |
| 82 | Ethan Clark | 7 | 2016-2018 | |
| 82 | Adrian Del Moral | 7 | 2020-2022 | |
| 82 | Trey Dombroski# | 7 | 2024-2024 | |
| 82 | Spencer Giesting# | 7 | 2023-2024 | |
| 82 | Luis Heredia | 7 | 2013-2013 | |
| 82 | Leonard Hollins | 7 | 2013-2016 | |
| 82 | Clinton Hollon | 7 | 2015-2017 | |
| 82 | Jason Hoppe | 7 | 2015-2016 | |
| 82 | Jimmy Kingsbury# | 7 | 2024-2024 | |
| 82 | Lucas Lanphere | 7 | 2014-2017 | |
| 82 | Conor Larkin# | 7 | 2022-2023 | |
| 82 | Kyle Leahy# | 7 | 2022-2022 | |
| 82 | Michael Limoncelli# | 7 | 2020-2024 | |
| 82 | Evan Lumbert | 7 | 2020-2023 | |
| 82 | Alec Mills# | 7 | 2013-2013 | |
| 82 | Jacob Morris | 7 | 2016-2019 |
