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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# | 39 | 2016-2026 | |
| 5 | Brad Bergesen | 37 | 2013-2016 | |
| 6 | Justin Dunn# | 36 | 2018-2026 | |
| 7 | Ryan Carpenter# | 34 | 2013-2023 | |
| 8 | Mark Appel | 33 | 2015-2018 | |
| 8 | Drew Rucinski# | 33 | 2021-2026 | |
| 10 | Logan Darnell | 31 | 2014-2023 | |
| 10 | Brady Lail | 31 | 2016-2020 | |
| 12 | Brett Kerry# | 30 | 2022-2026 | |
| 13 | Tim Melville | 29 | 2013-2020 | |
| 14 | David Buchanan# | 28 | 2013-2023 | |
| 14 | Stephen Tarpley# | 28 | 2020-2026 | |
| 16 | Connor Seabold# | 27 | 2019-2025 | |
| 17 | Luke Bard | 25 | 2015-2021 | |
| 17 | Marcelo Martinez# | 25 | 2020-2026 | |
| 19 | Tejay Antone# | 24 | 2018-2024 | |
| 19 | Michael Kopech# | 24 | 2018-2020 | |
| 19 | Luis Madero# | 24 | 2020-2025 | |
| 19 | Patrick Monteverde# | 24 | 2024-2026 | |
| 23 | 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 | Charlie Barnes# | 18 | 2020-2026 | |
| 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 | |
| 43 | Joan Adon# | 17 | 2020-2026 | |
| 43 | Pierce Johnson# | 17 | 2015-2017 | |
| 43 | Pat Light | 17 | 2016-2019 | |
| 43 | Zac Lowther# | 17 | 2020-2025 | |
| 43 | Tyler Mattison# | 17 | 2024-2026 | |
| 43 | Denyi Reyes# | 17 | 2022-2024 | |
| 49 | Buddy Boshers | 16 | 2014-2015 | |
| 49 | Josiah Gray# | 16 | 2020-2021 | |
| 49 | Steve Hathaway | 16 | 2017-2021 | |
| 49 | Edgar Ibarra | 16 | 2014-2015 | |
| 49 | James Naile# | 16 | 2018-2025 | |
| 49 | Enoli Paredes# | 16 | 2021-2024 | |
| 49 | Roniel Raudes# | 16 | 2018-2025 | |
| 49 | Joander Suarez# | 16 | 2024-2026 | |
| 49 | Trenton Wallace# | 16 | 2024-2025 | |
| 49 | Noah Zavolas# | 16 | 2022-2025 | |
| 59 | Albert Abreu# | 15 | 2018-2020 | |
| 59 | Orangel Arenas | 15 | 2013-2016 | |
| 59 | Dan Burawa | 15 | 2014-2016 | |
| 59 | Tim Cooney | 15 | 2014-2018 | |
| 59 | Jorge De Leon | 15 | 2013-2017 | |
| 59 | Derek Eitel | 15 | 2013-2017 | |
| 59 | Jeff Inman | 15 | 2013-2016 | |
| 59 | Sam McWilliams | 15 | 2021-2022 | |
| 59 | Angel Perdomo# | 15 | 2019-2023 | |
| 59 | Connor Phillips# | 15 | 2023-2025 | |
| 59 | Matt Purke | 15 | 2013-2017 | |
| 59 | Sal Romano# | 15 | 2016-2026 | |
| 59 | Atahualpa Severino | 15 | 2013-2018 | |
| 59 | Dylan TeBrake# | 15 | 2024-2026 | |
| 59 | Cesar Vargas | 15 | 2016-2018 | |
| 59 | Sam Wolff | 15 | 2017-2024 | |
| 75 | Spencer Arrighetti# | 14 | 2026-2026 | |
| 75 | Sam Bachman# | 14 | 2024-2026 | |
| 75 | Nolan Blackwood# | 14 | 2019-2025 | |
| 75 | Miguel Celestino | 14 | 2014-2016 | |
| 75 | Noah Davis# | 14 | 2026-2026 | |
| 75 | Dayan Diaz | 14 | 2016-2022 | |
| 75 | Nick Economos | 14 | 2020-2022 | |
| 75 | Harol Gonzalez# | 14 | 2020-2025 | |
| 75 | Jose M. Marte# | 14 | 2022-2026 | |
| 75 | Juan Minaya | 14 | 2019-2024 | |
| 75 | Nestor Molina | 14 | 2012-2014 | |
| 75 | Mikey O'Brien | 14 | 2014-2016 | |
| 75 | Joe Palumbo# | 14 | 2022-2025 | |
| 75 | Brooks Pounders | 14 | 2016-2021 | |
| 75 | Tate Scioneaux | 14 | 2016-2021 | |
| 75 | Tarik Skubal# | 14 | 2020-2021 | |
| 75 | Drew Storen | 14 | 2019-2022 | |
| 92 | Jesse Biddle | 13 | 2014-2020 | |
| 92 | Gerardo Carrillo# | 13 | 2023-2026 | |
| 92 | Andrew Chafin# | 13 | 2013-2014 | |
| 92 | Sam Delaplane# | 13 | 2020-2023 | |
| 92 | Montana DuRapau | 13 | 2020-2023 | |
| 92 | Roenis Elias | 13 | 2016-2023 | |
| 92 | Robbie Erlin | 13 | 2013-2017 | |
| 92 | Kyle Friedrichs | 13 | 2018-2023 | |
| 92 | Ian Gardeck | 13 | 2017-2021 |
