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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Casey Kelly# | 46 | 2017-2024 | |
| 2 | Odrisamer Despaigne# | 41 | 2021-2023 | |
| 2 | Eric Hacker | 41 | 2016-2020 | |
| 4 | William Cuevas# | 38 | 2016-2026 | |
| 5 | Brad Bergesen | 37 | 2013-2016 | |
| 6 | Ryan Carpenter# | 34 | 2013-2023 | |
| 7 | Mark Appel | 33 | 2015-2018 | |
| 7 | Justin Dunn# | 33 | 2018-2026 | |
| 9 | Drew Rucinski# | 32 | 2021-2026 | |
| 10 | Logan Darnell | 31 | 2014-2023 | |
| 10 | Brady Lail | 31 | 2016-2020 | |
| 12 | Tim Melville | 29 | 2013-2020 | |
| 13 | David Buchanan# | 28 | 2013-2023 | |
| 13 | Stephen Tarpley# | 28 | 2020-2026 | |
| 15 | Connor Seabold# | 27 | 2019-2025 | |
| 16 | Luke Bard | 25 | 2015-2021 | |
| 17 | Tejay Antone# | 24 | 2018-2024 | |
| 17 | Brett Kerry# | 24 | 2022-2026 | |
| 17 | Michael Kopech# | 24 | 2018-2020 | |
| 17 | Luis Madero# | 24 | 2020-2025 | |
| 21 | Marcelo Martinez# | 23 | 2020-2026 | |
| 21 | Patrick Monteverde# | 23 | 2024-2026 | |
| 21 | Ryan Yarbrough# | 23 | 2017-2020 | |
| 24 | Justin Donatella | 22 | 2019-2023 | |
| 24 | Carl Edwards Jr.# | 22 | 2015-2016 | |
| 24 | Sam Gaviglio | 22 | 2014-2017 | |
| 24 | Riley O'Brien# | 22 | 2021-2025 | |
| 28 | Adalberto Mejia | 21 | 2015-2017 | |
| 29 | Yimi Garcia# | 20 | 2014-2020 | |
| 29 | Alex Meyer | 20 | 2013-2017 | |
| 29 | Nick Travieso | 20 | 2014-2021 | |
| 32 | Mike Foltynewicz | 19 | 2014-2015 | |
| 32 | Marcus Stroman# | 19 | 2013-2014 | |
| 32 | Brandon Waddell# | 19 | 2018-2024 | |
| 35 | Randy Bell# | 18 | 2020-2023 | |
| 35 | Sean Mellen# | 18 | 2023-2025 | |
| 35 | Williams Perez | 18 | 2020-2021 | |
| 35 | Konnor Pilkington# | 18 | 2020-2025 | |
| 35 | Austin Pruitt# | 18 | 2017-2017 | |
| 35 | Tyler Thornburg | 18 | 2013-2014 | |
| 35 | Jeff Urlaub | 18 | 2013-2016 | |
| 42 | Pierce Johnson# | 17 | 2015-2017 | |
| 42 | Pat Light | 17 | 2016-2019 | |
| 42 | Zac Lowther# | 17 | 2020-2025 | |
| 42 | Tyler Mattison# | 17 | 2024-2026 | |
| 42 | Denyi Reyes# | 17 | 2022-2024 | |
| 47 | Buddy Boshers | 16 | 2014-2015 | |
| 47 | Josiah Gray# | 16 | 2020-2021 | |
| 47 | Steve Hathaway | 16 | 2017-2021 | |
| 47 | Edgar Ibarra | 16 | 2014-2015 | |
| 47 | James Naile# | 16 | 2018-2025 | |
| 47 | Enoli Paredes# | 16 | 2021-2024 | |
| 47 | Roniel Raudes# | 16 | 2018-2025 | |
| 47 | Trenton Wallace# | 16 | 2024-2025 | |
| 47 | Noah Zavolas# | 16 | 2022-2025 | |
| 56 | Albert Abreu# | 15 | 2018-2020 | |
| 56 | Orangel Arenas | 15 | 2013-2016 | |
| 56 | Charlie Barnes# | 15 | 2020-2026 | |
| 56 | Dan Burawa | 15 | 2014-2016 | |
| 56 | Tim Cooney | 15 | 2014-2018 | |
| 56 | Jorge De Leon | 15 | 2013-2017 | |
| 56 | Derek Eitel | 15 | 2013-2017 | |
| 56 | Jeff Inman | 15 | 2013-2016 | |
| 56 | Sam McWilliams | 15 | 2021-2022 | |
| 56 | Angel Perdomo# | 15 | 2019-2023 | |
| 56 | Connor Phillips# | 15 | 2023-2025 | |
| 56 | Matt Purke | 15 | 2013-2017 | |
| 56 | Sal Romano# | 15 | 2016-2026 | |
| 56 | Atahualpa Severino | 15 | 2013-2018 | |
| 56 | Cesar Vargas | 15 | 2016-2018 | |
| 56 | Sam Wolff | 15 | 2017-2024 | |
| 72 | Nolan Blackwood# | 14 | 2019-2025 | |
| 72 | Miguel Celestino | 14 | 2014-2016 | |
| 72 | Dayan Diaz | 14 | 2016-2022 | |
| 72 | Nick Economos | 14 | 2020-2022 | |
| 72 | Harol Gonzalez# | 14 | 2020-2025 | |
| 72 | Juan Minaya | 14 | 2019-2024 | |
| 72 | Nestor Molina | 14 | 2012-2014 | |
| 72 | Mikey O'Brien | 14 | 2014-2016 | |
| 72 | Joe Palumbo# | 14 | 2022-2025 | |
| 72 | Brooks Pounders | 14 | 2016-2021 | |
| 72 | Tate Scioneaux | 14 | 2016-2021 | |
| 72 | Tarik Skubal# | 14 | 2020-2021 | |
| 72 | Drew Storen | 14 | 2019-2022 | |
| 72 | Dylan TeBrake# | 14 | 2024-2026 | |
| 86 | Jesse Biddle | 13 | 2014-2020 | |
| 86 | Andrew Chafin# | 13 | 2013-2014 | |
| 86 | Sam Delaplane# | 13 | 2020-2023 | |
| 86 | Montana DuRapau | 13 | 2020-2023 | |
| 86 | Roenis Elias | 13 | 2016-2023 | |
| 86 | Robbie Erlin | 13 | 2013-2017 | |
| 86 | Kyle Friedrichs | 13 | 2018-2023 | |
| 86 | Ian Gardeck | 13 | 2017-2021 | |
| 86 | Will Gilbert | 13 | 2018-2020 | |
| 86 | Tyler Glasnow# | 13 | 2016-2021 | |
| 86 | Cole Gordon | 13 | 2022-2023 | |
| 86 | Cody Martin | 13 | 2013-2015 | |
| 86 | Nick Nelson# | 13 | 2019-2024 | |
| 86 | Zachary Nuding | 13 | 2013-2015 | |
| 86 | Pierson Ohl# | 13 | 2025-2025 |
