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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ryan Weber | 50 | 2016-2023 | |
| 2 | Kyle Weiland | 49 | 2013-2017 | |
| 3 | Eric Jokisch# | 47 | 2018-2023 | |
| 3 | Brett Oberholtzer | 47 | 2013-2021 | |
| 5 | Christian Friedrich | 46 | 2014-2021 | |
| 6 | Luis Mendoza | 44 | 2013-2018 | |
| 7 | Ty Blach# | 42 | 2014-2023 | |
| 7 | Marcus Walden | 42 | 2015-2024 | |
| 9 | Carlos Rodon# | 41 | 2016-2019 | |
| 10 | Tyler Beede# | 39 | 2017-2025 | |
| 10 | Dustin McGowan | 39 | 2014-2016 | |
| 12 | Miguel A. Gonzalez | 38 | 2014-2018 | |
| 12 | Austin Pruitt# | 38 | 2017-2024 | |
| 14 | Cory Gearrin | 37 | 2013-2020 | |
| 14 | Jorge Lopez# | 37 | 2015-2020 | |
| 14 | Cody Poteet# | 37 | 2019-2024 | |
| 14 | Andrew Suarez# | 37 | 2018-2022 | |
| 18 | Blake Beavan | 36 | 2013-2018 | |
| 18 | Nicholas Kingham | 36 | 2016-2022 | |
| 20 | Adam Plutko# | 35 | 2017-2024 | |
| 21 | Aaron Brooks# | 34 | 2015-2025 | |
| 21 | Sal Romano# | 34 | 2017-2025 | |
| 21 | Alex White | 34 | 2013-2017 | |
| 21 | Asher Wojciechowski | 34 | 2014-2024 | |
| 25 | Jake Thompson | 33 | 2016-2020 | |
| 25 | Alex Young# | 33 | 2017-2024 | |
| 27 | Anthony Cingrani | 32 | 2013-2022 | |
| 27 | Cory Luebke | 32 | 2013-2016 | |
| 27 | Max Povse | 32 | 2018-2021 | |
| 27 | Andre Rienzo | 32 | 2013-2016 | |
| 27 | Tanner Roark | 32 | 2013-2016 | |
| 32 | Glenn Sparkman | 31 | 2017-2023 | |
| 33 | Joe Gunkel | 30 | 2018-2021 | |
| 33 | Daniel Mengden# | 30 | 2017-2024 | |
| 33 | Ross Ohlendorf | 30 | 2013-2016 | |
| 33 | Rob Zastryzny# | 30 | 2018-2024 | |
| 37 | Austin Adams | 29 | 2015-2020 | |
| 37 | Cooper Criswell# | 29 | 2022-2025 | |
| 37 | Jerad Eickhoff | 29 | 2015-2021 | |
| 37 | Conor Fisk | 29 | 2019-2021 | |
| 37 | Cody Reed# | 29 | 2017-2025 | |
| 42 | Vidal Nuno | 28 | 2013-2020 | |
| 42 | Chris Rusin | 28 | 2013-2015 | |
| 44 | Jose Alvarez | 27 | 2015-2021 | |
| 44 | Ryan Feierabend | 27 | 2011-2021 | |
| 44 | Daulton Jefferies# | 27 | 2020-2025 | |
| 44 | Jeff Manship | 27 | 2013-2019 | |
| 44 | Steve Matz# | 27 | 2015-2019 | |
| 44 | Johan Oviedo# | 27 | 2021-2024 | |
| 44 | James Paxton# | 27 | 2014-2016 | |
| 44 | Jose A. Ramirez | 27 | 2014-2019 | |
| 52 | Buddy Boshers | 26 | 2016-2021 | |
| 52 | Chris Hernandez | 26 | 2013-2016 | |
| 52 | Adrian Houser# | 26 | 2017-2025 | |
| 52 | Kolton Mahoney | 26 | 2020-2022 | |
| 52 | Joel Payamps# | 26 | 2019-2024 | |
| 52 | A.J. Puk# | 26 | 2019-2021 | |
| 52 | Trevor Williams# | 26 | 2015-2024 | |
| 59 | David Buchanan# | 25 | 2015-2021 | |
| 59 | Taylor Clarke# | 25 | 2021-2025 | |
| 59 | Derek Law# | 25 | 2016-2024 | |
| 59 | Matt Manning# | 25 | 2019-2023 | |
| 59 | Shairon Martis | 25 | 2013-2017 | |
| 59 | Erik Swanson# | 25 | 2019-2025 | |
| 59 | Trent Thornton# | 25 | 2018-2025 | |
| 59 | Matthew Tomshaw | 25 | 2017-2022 | |
| 59 | Jose Urena# | 25 | 2015-2025 | |
| 59 | Kirby Yates# | 25 | 2014-2019 | |
| 69 | Albert Abreu# | 24 | 2016-2024 | |
| 69 | Christian Binford | 24 | 2017-2021 | |
| 69 | Archie Bradley | 24 | 2014-2016 | |
| 69 | Robbie Erlin# | 24 | 2013-2018 | |
| 69 | Brady Singer# | 24 | 2020-2024 | |
| 69 | Chase Whitley | 24 | 2014-2019 | |
| 69 | Adam Wilk | 24 | 2014-2018 | |
| 76 | Tejay Antone# | 23 | 2020-2023 | |
| 76 | Shawn Armstrong# | 23 | 2017-2023 | |
| 76 | Manny Banuelos# | 23 | 2017-2024 | |
| 76 | Sean Gilmartin | 23 | 2017-2023 | |
| 76 | Ryan Helsley# | 23 | 2019-2022 | |
| 76 | James Hoyt | 23 | 2016-2021 | |
| 76 | Mickey Jannis | 23 | 2018-2022 | |
| 76 | Jason Jester | 23 | 2016-2021 | |
| 76 | Spenser Watkins# | 23 | 2022-2025 | |
| 76 | Ross Wolf | 23 | 2013-2016 | |
| 86 | Yadier Alvarez# | 22 | 2019-2025 | |
| 86 | Jake Barrett | 22 | 2014-2020 | |
| 86 | Davis Daniel# | 22 | 2022-2025 | |
| 86 | Dane Dunning# | 22 | 2019-2022 | |
| 86 | Josh Fleming# | 22 | 2020-2025 | |
| 86 | Luiz Gohara | 22 | 2018-2021 | |
| 86 | Nick Lodolo# | 22 | 2020-2024 | |
| 86 | Cody Martin | 22 | 2015-2018 | |
| 86 | Casey Mize# | 22 | 2020-2022 | |
| 86 | Jon Moscot | 22 | 2015-2019 | |
| 86 | D.J. Myers | 22 | 2020-2022 | |
| 86 | Luis Perdomo# | 22 | 2017-2018 | |
| 86 | Brooks Pounders | 22 | 2015-2020 | |
| 86 | Nick Tropeano | 22 | 2016-2023 | |
| 86 | Josh Winder# | 22 | 2022-2024 |
