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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ivan Pineyro | 42 | 2014-2019 | |
| 2 | Tommy Bergjans | 32 | 2016-2019 | |
| 3 | Michael McCarthy | 31 | 2013-2017 | |
| 3 | Benino Pruneda | 31 | 2013-2016 | |
| 5 | Juan Hillman# | 29 | 2020-2025 | |
| 6 | Wilking Rodriguez# | 28 | 2013-2021 | |
| 6 | Aaron Shortridge# | 28 | 2020-2026 | |
| 8 | Luis Madero# | 27 | 2020-2026 | |
| 8 | Josh Poytress | 27 | 2013-2017 | |
| 8 | Niklas Stephenson | 27 | 2016-2023 | |
| 11 | Taylor Hill | 25 | 2013-2019 | |
| 11 | Ryan O'Sullivan | 25 | 2014-2018 | |
| 11 | Austin Wright | 25 | 2014-2016 | |
| 14 | Brandon Gold | 24 | 2018-2022 | |
| 14 | Sam Hentges# | 24 | 2017-2021 | |
| 14 | Garrett Nuss | 24 | 2014-2017 | |
| 17 | Garrett Davila# | 23 | 2019-2024 | |
| 17 | Mark Reyes | 23 | 2017-2019 | |
| 17 | Tom Robson | 23 | 2015-2022 | |
| 17 | Randy Rosario | 23 | 2017-2021 | |
| 17 | Matt Vogel# | 23 | 2020-2026 | |
| 22 | Scott Copeland | 22 | 2013-2018 | |
| 22 | Will Lamb | 22 | 2013-2016 | |
| 22 | Luis Palacios# | 22 | 2023-2026 | |
| 25 | Pedro Araujo | 21 | 2016-2021 | |
| 25 | Ryan Bean | 21 | 2013-2017 | |
| 25 | Cole Coshow | 21 | 2017-2020 | |
| 25 | Michael Murray | 21 | 2017-2021 | |
| 25 | Josh Osich | 21 | 2013-2021 | |
| 25 | Joey Wentz# | 21 | 2019-2021 | |
| 31 | Matthew Boyd# | 20 | 2014-2016 | |
| 31 | Brock Burke# | 20 | 2019-2021 | |
| 31 | Zach Cates | 20 | 2014-2016 | |
| 31 | Taylor Cole | 20 | 2013-2015 | |
| 31 | Ian Gibaut# | 20 | 2018-2022 | |
| 31 | Josh Hendrickson# | 20 | 2021-2025 | |
| 31 | Joshua Smith | 20 | 2013-2014 | |
| 38 | Denny Brady# | 19 | 2019-2024 | |
| 38 | Frank Garces | 19 | 2013-2018 | |
| 38 | John Niggli | 19 | 2013-2016 | |
| 38 | Cody Sedlock# | 19 | 2018-2021 | |
| 38 | Dillon Tate# | 19 | 2016-2020 | |
| 38 | Eduardo Vera | 19 | 2018-2021 | |
| 44 | Genesis Cabrera# | 18 | 2018-2026 | |
| 44 | Malcolm Culver | 18 | 2014-2015 | |
| 44 | Trevor Frank | 18 | 2017-2021 | |
| 44 | Jarlin Garcia# | 18 | 2014-2019 | |
| 44 | Brennan Hanifee# | 18 | 2019-2024 | |
| 44 | Tyler Herb | 18 | 2017-2021 | |
| 44 | Ronald Herrera# | 18 | 2018-2022 | |
| 44 | Corey Littrell | 18 | 2016-2018 | |
| 44 | Kyle Luckham# | 18 | 2023-2026 | |
| 44 | Rafael Martin | 18 | 2013-2019 | |
| 44 | Benton Moss | 18 | 2016-2020 | |
| 44 | Eric Skoglund | 18 | 2016-2020 | |
| 44 | Noah Zavolas# | 18 | 2023-2026 | |
| 57 | Sean Brady | 17 | 2018-2021 | |
| 57 | Tyler DeLoach | 17 | 2013-2017 | |
| 57 | Dustin Driver | 17 | 2016-2019 | |
| 57 | Joe Gatto | 17 | 2019-2022 | |
| 57 | David Ledbetter | 17 | 2015-2018 | |
| 57 | Tim Melville | 17 | 2019-2020 | |
| 57 | Greg Nappo | 17 | 2014-2016 | |
| 57 | Braden Olthoff# | 17 | 2023-2024 | |
| 57 | Kenny Rosenberg# | 17 | 2018-2026 | |
| 57 | Austin Smith | 17 | 2019-2024 | |
| 57 | Andrew Summerville | 17 | 2019-2021 | |
| 57 | Troy Watson# | 17 | 2021-2026 | |
| 57 | Collin Wiles# | 17 | 2019-2026 | |
| 57 | Alex Wimmers | 17 | 2014-2018 | |
| 71 | Dakota Bacus | 16 | 2015-2021 | |
| 71 | Shane Drohan# | 16 | 2023-2023 | |
| 71 | Gray Fenter | 16 | 2018-2021 | |
| 71 | Josh Graham | 16 | 2018-2021 | |
| 71 | Carlos A. Guzman# | 16 | 2021-2025 | |
| 71 | Trey Killian | 16 | 2017-2018 | |
| 71 | Jared Lakind | 16 | 2014-2017 | |
| 71 | Hector Lujan# | 16 | 2016-2026 | |
| 71 | Scott Lyman | 16 | 2014-2017 | |
| 71 | Bryan Mitchell | 16 | 2021-2023 | |
| 71 | Taylor Rashi# | 16 | 2022-2026 | |
| 71 | Enny Romero | 16 | 2013-2020 | |
| 71 | Carlos Vargas# | 16 | 2021-2025 | |
| 71 | Nolan Watson# | 16 | 2019-2026 | |
| 85 | Xavier Altamirano | 15 | 2019-2020 | |
| 85 | James Buckelew | 15 | 2018-2020 | |
| 85 | Ryan Clark | 15 | 2018-2021 | |
| 85 | Calvin Coker# | 15 | 2020-2026 | |
| 85 | Tanner Dodson# | 15 | 2020-2025 | |
| 85 | Caleb Frare | 15 | 2016-2018 | |
| 85 | Tink Hence# | 15 | 2023-2025 | |
| 85 | Michael Kelly# | 15 | 2017-2023 | |
| 85 | Zach King# | 15 | 2022-2025 | |
| 85 | Yeison Medina | 15 | 2019-2021 | |
| 85 | Wills Montgomerie# | 15 | 2020-2025 | |
| 85 | Fernando Romero# | 15 | 2018-2025 | |
| 85 | Kyle Ryan | 15 | 2014-2015 | |
| 85 | Peter Tago | 15 | 2014-2022 | |
| 85 | Shawn Teufel | 15 | 2013-2016 | |
| 100 | Jesse Beal | 14 | 2015-2015 |
