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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Odrisamer Despaigne# | 41 | 2021-2023 | |
| 1 | Eric Hacker | 41 | 2016-2020 | |
| 3 | Brad Bergesen | 37 | 2013-2016 | |
| 4 | Casey Kelly# | 35 | 2017-2023 | |
| 5 | Ryan Carpenter# | 34 | 2013-2023 | |
| 6 | Mark Appel | 33 | 2015-2018 | |
| 7 | Logan Darnell# | 31 | 2014-2023 | |
| 7 | Brady Lail | 31 | 2016-2020 | |
| 9 | Joshua Lucas# | 29 | 2018-2023 | |
| 9 | Tim Melville | 29 | 2013-2020 | |
| 11 | David Buchanan# | 28 | 2013-2023 | |
| 12 | Bubba Derby# | 27 | 2018-2023 | |
| 13 | Luke Bard | 25 | 2015-2021 | |
| 13 | William Cuevas# | 25 | 2016-2023 | |
| 15 | Michael Kopech# | 24 | 2018-2020 | |
| 15 | Luis Madero# | 24 | 2020-2023 | |
| 17 | Nick Greenwood# | 23 | 2014-2022 | |
| 17 | Felix Paulino# | 23 | 2019-2023 | |
| 17 | Ryan Yarbrough# | 23 | 2017-2020 | |
| 20 | Justin Donatella# | 22 | 2019-2023 | |
| 20 | Carl Edwards Jr.# | 22 | 2015-2016 | |
| 20 | Sam Gaviglio | 22 | 2014-2017 | |
| 20 | Franklin Perez# | 22 | 2018-2023 | |
| 24 | Adalberto Mejia | 21 | 2015-2017 | |
| 24 | Felipe Vazquez# | 21 | 2014-2015 | |
| 26 | Yimi Garcia# | 20 | 2014-2020 | |
| 26 | Connor Johnstone# | 20 | 2020-2023 | |
| 26 | Alex Meyer | 20 | 2013-2017 | |
| 26 | Nick Travieso | 20 | 2014-2021 | |
| 30 | Tejay Antone# | 19 | 2018-2023 | |
| 30 | Mike Foltynewicz | 19 | 2014-2015 | |
| 30 | Riley O'Brien# | 19 | 2021-2023 | |
| 30 | Connor Seabold# | 19 | 2019-2020 | |
| 30 | Marcus Stroman# | 19 | 2013-2014 | |
| 30 | Brandon Waddell# | 19 | 2018-2023 | |
| 36 | Jason Bahr# | 18 | 2019-2023 | |
| 36 | Randy Bell# | 18 | 2020-2023 | |
| 36 | Marcelo Martinez# | 18 | 2020-2023 | |
| 36 | Williams Perez# | 18 | 2020-2021 | |
| 36 | Austin Pruitt# | 18 | 2017-2017 | |
| 36 | Tyler Thornburg | 18 | 2013-2014 | |
| 36 | Jeff Urlaub | 18 | 2013-2016 | |
| 43 | Austin Hutchison# | 17 | 2019-2022 | |
| 43 | Pierce Johnson# | 17 | 2015-2017 | |
| 43 | Pat Light | 17 | 2016-2019 | |
| 43 | Zac Lowther# | 17 | 2020-2023 | |
| 43 | Kade McClure# | 17 | 2022-2023 | |
| 48 | Buddy Boshers | 16 | 2014-2015 | |
| 48 | Justin Dunn# | 16 | 2018-2022 | |
| 48 | Josiah Gray# | 16 | 2020-2021 | |
| 48 | Steve Hathaway | 16 | 2017-2021 | |
| 48 | Edgar Ibarra | 16 | 2014-2015 | |
| 48 | Michael Mariot# | 16 | 2013-2015 | |
| 48 | Stephen Tarpley# | 16 | 2020-2023 | |
| 55 | Albert Abreu# | 15 | 2018-2020 | |
| 55 | Orangel Arenas | 15 | 2013-2016 | |
| 55 | Dan Burawa | 15 | 2014-2016 | |
| 55 | P.J. Conlon# | 15 | 2018-2023 | |
| 55 | Tim Cooney | 15 | 2014-2018 | |
| 55 | Jorge De Leon | 15 | 2013-2017 | |
| 55 | Derek Eitel | 15 | 2013-2017 | |
| 55 | Jeff Inman | 15 | 2013-2016 | |
| 55 | Sam McWilliams# | 15 | 2021-2022 | |
| 55 | Angel Perdomo# | 15 | 2019-2023 | |
| 55 | Matt Purke | 15 | 2013-2017 | |
| 55 | Atahualpa Severino | 15 | 2013-2018 | |
| 55 | Cesar Vargas# | 15 | 2016-2018 | |
| 68 | Charlie Barnes# | 14 | 2020-2023 | |
| 68 | Miguel Celestino | 14 | 2014-2016 | |
| 68 | Dayan Diaz | 14 | 2016-2022 | |
| 68 | Nick Economos# | 14 | 2020-2022 | |
| 68 | Colton Hathcock# | 14 | 2019-2022 | |
| 68 | Juan Minaya# | 14 | 2019-2023 | |
| 68 | Nestor Molina | 14 | 2012-2014 | |
| 68 | Mikey O'Brien | 14 | 2014-2016 | |
| 68 | Brooks Pounders | 14 | 2016-2021 | |
| 68 | Sal Romano# | 14 | 2016-2017 | |
| 68 | Tate Scioneaux# | 14 | 2016-2021 | |
| 68 | Tarik Skubal# | 14 | 2020-2021 | |
| 68 | Drew Storen | 14 | 2019-2022 | |
| 81 | Jesse Biddle# | 13 | 2014-2020 | |
| 81 | Nolan Blackwood | 13 | 2019-2023 | |
| 81 | Andrew Chafin# | 13 | 2013-2014 | |
| 81 | Sam Delaplane# | 13 | 2020-2023 | |
| 81 | Montana DuRapau# | 13 | 2020-2023 | |
| 81 | Roenis Elias | 13 | 2016-2023 | |
| 81 | Robbie Erlin# | 13 | 2013-2017 | |
| 81 | Kyle Friedrichs | 13 | 2018-2023 | |
| 81 | Ian Gardeck | 13 | 2017-2021 | |
| 81 | Will Gilbert | 13 | 2018-2020 | |
| 81 | Tyler Glasnow# | 13 | 2016-2021 | |
| 81 | Cole Gordon# | 13 | 2022-2023 | |
| 81 | Brad Hand# | 13 | 2016-2016 | |
| 81 | Cody Martin | 13 | 2013-2015 | |
| 81 | Zachary Nuding | 13 | 2013-2015 | |
| 81 | Colin Rea# | 13 | 2020-2021 | |
| 81 | Andrew Sopko# | 13 | 2019-2023 | |
| 81 | Cody Stull | 13 | 2018-2020 | |
| 81 | Domingo Tapia# | 13 | 2019-2023 | |
| 81 | Aaron Thompson | 13 | 2013-2015 |
