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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Erick Leal# | 38 | 2018-2021 | |
| 2 | Jeff Ames | 36 | 2014-2017 | |
| 3 | Tanner Peters | 34 | 2013-2016 | |
| 4 | Mason Radeke | 33 | 2014-2018 | |
| 5 | Parker Markel | 32 | 2013-2016 | |
| 6 | Jordan Pries | 30 | 2013-2016 | |
| 6 | Jake Stinnett | 30 | 2017-2021 | |
| 8 | Denyi Reyes# | 29 | 2020-2022 | |
| 9 | Jose Taveras | 28 | 2019-2023 | |
| 10 | Gus Varland# | 25 | 2020-2022 | |
| 11 | Matt Brazis | 24 | 2013-2016 | |
| 11 | Manaure Martinez | 24 | 2014-2016 | |
| 13 | Parker Bridwell | 23 | 2014-2022 | |
| 13 | Ian Gardeck | 23 | 2014-2019 | |
| 13 | Ryan Kellogg | 23 | 2017-2021 | |
| 13 | Brendon Little# | 23 | 2018-2022 | |
| 17 | Chase Huchingson | 22 | 2013-2016 | |
| 18 | Bear Bellomy# | 21 | 2022-2026 | |
| 18 | Josh Winder# | 21 | 2020-2021 | |
| 20 | Jonathan Dziedzic | 20 | 2014-2015 | |
| 20 | Silfredo Garcia | 20 | 2014-2016 | |
| 20 | Max Lazar# | 20 | 2018-2022 | |
| 20 | Jack Leftwich# | 20 | 2023-2026 | |
| 20 | Elvis Luciano# | 20 | 2019-2026 | |
| 25 | Jayson Aquino | 19 | 2014-2016 | |
| 25 | Andy Beltre | 19 | 2014-2016 | |
| 25 | Gustavo Gomez | 19 | 2014-2016 | |
| 25 | Nolan Hoffman# | 19 | 2020-2026 | |
| 25 | Dallas Litscher | 19 | 2019-2022 | |
| 25 | Mike Ruff | 19 | 2020-2024 | |
| 25 | Noe Toribio# | 19 | 2022-2026 | |
| 32 | Valente Bellozo# | 18 | 2023-2024 | |
| 32 | Alex Black | 18 | 2014-2017 | |
| 32 | Bryce Bonnin# | 18 | 2023-2026 | |
| 32 | Kannon Kemp# | 18 | 2025-2026 | |
| 32 | Kyle Larsen# | 18 | 2023-2026 | |
| 32 | Trey McGough# | 18 | 2022-2026 | |
| 32 | Ronald Pena | 18 | 2016-2020 | |
| 32 | John Rooney# | 18 | 2020-2026 | |
| 32 | Chris Rowley | 18 | 2017-2021 | |
| 32 | Victor Santos# | 18 | 2022-2026 | |
| 32 | Brian Shaffer | 18 | 2019-2021 | |
| 32 | Jesus Tinoco# | 18 | 2019-2023 | |
| 44 | Omar Cruz# | 17 | 2022-2026 | |
| 44 | Tommy Doyle# | 17 | 2018-2024 | |
| 44 | Ismael Guillon | 17 | 2017-2019 | |
| 44 | Kyle Hunter | 17 | 2013-2017 | |
| 44 | Scott McGough# | 17 | 2013-2015 | |
| 44 | Robinson Ortiz# | 17 | 2020-2025 | |
| 44 | Jack Perkins# | 17 | 2023-2025 | |
| 44 | Carlson Reed# | 17 | 2025-2026 | |
| 44 | Dae-Eun Rhee | 17 | 2013-2014 | |
| 44 | Kendall Williams# | 17 | 2022-2025 | |
| 54 | Yovanny Cruz# | 16 | 2021-2026 | |
| 54 | Robbie Hitt# | 16 | 2018-2023 | |
| 54 | Jon Olsen# | 16 | 2022-2025 | |
| 54 | Eduardo Rodriguez# | 16 | 2014-2015 | |
| 54 | Chad Thompson | 16 | 2014-2016 | |
| 54 | Konner Wade# | 16 | 2014-2024 | |
| 60 | Solomon Bates | 15 | 2020-2022 | |
| 60 | Cooper Benson# | 15 | 2022-2025 | |
| 60 | Jesse Biddle | 15 | 2013-2013 | |
| 60 | Tyler Dyson# | 15 | 2022-2024 | |
| 60 | Jordan Johnson | 15 | 2017-2020 | |
| 60 | Brian Miller | 15 | 2017-2019 | |
| 60 | Chris Rodriguez# | 15 | 2019-2025 | |
| 60 | Timothy Shibuya | 15 | 2014-2018 | |
| 68 | Braxton Ashcraft# | 14 | 2022-2026 | |
| 68 | Kyle Bartsch | 14 | 2014-2017 | |
| 68 | Riley Davis# | 14 | 2023-2025 | |
| 68 | Connor Grey | 14 | 2018-2021 | |
| 68 | Casey Harman | 14 | 2013-2018 | |
| 68 | Anthony Misiewicz# | 14 | 2019-2020 | |
| 68 | Jorge Ortega | 14 | 2017-2019 | |
| 68 | Austin Roberts# | 14 | 2022-2025 | |
| 68 | Domingo Robles# | 14 | 2019-2020 | |
| 68 | Tony Santillan# | 14 | 2018-2020 | |
| 68 | Adam Scott | 14 | 2020-2021 | |
| 68 | Trent Szkutnik | 14 | 2016-2020 | |
| 68 | Spenser Watkins# | 14 | 2020-2026 | |
| 68 | Benjamin Wells | 14 | 2016-2017 | |
| 82 | Manny Banuelos | 13 | 2013-2013 | |
| 82 | Christian Cosby# | 13 | 2023-2024 | |
| 82 | Jacob Dahlstrand | 13 | 2015-2016 | |
| 82 | Luis Diaz | 13 | 2014-2014 | |
| 82 | Raul Fernandez | 13 | 2014-2017 | |
| 82 | William Fleming# | 13 | 2024-2025 | |
| 82 | Nick Fraze# | 13 | 2022-2026 | |
| 82 | Michael Fulmer# | 13 | 2013-2015 | |
| 82 | Michael Matuella | 13 | 2016-2022 | |
| 82 | Erling Moreno | 13 | 2019-2021 | |
| 82 | Kyle Nelson# | 13 | 2019-2022 | |
| 82 | Davis Palermo# | 13 | 2024-2026 | |
| 82 | Zach Schellenger | 13 | 2019-2022 | |
| 95 | Austin Becker# | 12 | 2023-2024 | |
| 95 | Robert Benincasa | 12 | 2014-2016 | |
| 95 | Mike Broadway | 12 | 2013-2015 | |
| 95 | Austin Cates# | 12 | 2025-2026 | |
| 95 | Gerald Garcia# | 12 | 2022-2024 | |
| 95 | Tyler Gray# | 12 | 2020-2025 |
