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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 | Tyler Beede# | 46 | 2017-2025 | |
| 5 | Christian Friedrich | 46 | 2014-2021 | |
| 7 | Ty Blach# | 45 | 2014-2025 | |
| 8 | Luis Mendoza | 44 | 2013-2018 | |
| 9 | Marcus Walden | 42 | 2015-2024 | |
| 10 | Carlos Rodon# | 41 | 2016-2019 | |
| 11 | Aaron Brooks# | 40 | 2015-2025 | |
| 12 | Dustin McGowan | 39 | 2014-2016 | |
| 13 | Miguel A. Gonzalez | 38 | 2014-2018 | |
| 13 | Austin Pruitt# | 38 | 2017-2024 | |
| 15 | Cory Gearrin | 37 | 2013-2020 | |
| 15 | Jorge Lopez# | 37 | 2015-2020 | |
| 15 | Cody Poteet# | 37 | 2019-2024 | |
| 15 | Andrew Suarez# | 37 | 2018-2022 | |
| 19 | Blake Beavan | 36 | 2013-2018 | |
| 19 | Nicholas Kingham | 36 | 2016-2022 | |
| 21 | Adam Plutko# | 35 | 2017-2024 | |
| 22 | Sal Romano# | 34 | 2017-2025 | |
| 22 | Alex White | 34 | 2013-2017 | |
| 22 | Asher Wojciechowski | 34 | 2014-2024 | |
| 25 | Adrian Houser# | 33 | 2017-2025 | |
| 25 | Jake Thompson | 33 | 2016-2020 | |
| 25 | Alex Young# | 33 | 2017-2024 | |
| 28 | Anthony Cingrani | 32 | 2013-2022 | |
| 28 | Cooper Criswell# | 32 | 2022-2025 | |
| 28 | Shawn Dubin# | 32 | 2022-2025 | |
| 28 | Daulton Jefferies# | 32 | 2020-2025 | |
| 28 | Cory Luebke | 32 | 2013-2016 | |
| 28 | Max Povse | 32 | 2018-2021 | |
| 28 | Andre Rienzo | 32 | 2013-2016 | |
| 28 | Tanner Roark | 32 | 2013-2016 | |
| 36 | Cody Reed# | 31 | 2017-2025 | |
| 36 | Glenn Sparkman | 31 | 2017-2023 | |
| 38 | Taylor Clarke# | 30 | 2021-2025 | |
| 38 | Davis Daniel# | 30 | 2022-2025 | |
| 38 | Joe Gunkel | 30 | 2018-2021 | |
| 38 | Daniel Mengden# | 30 | 2017-2024 | |
| 38 | Ross Ohlendorf | 30 | 2013-2016 | |
| 38 | Tyler Viza# | 30 | 2021-2025 | |
| 38 | Rob Zastryzny# | 30 | 2018-2025 | |
| 45 | Austin Adams | 29 | 2015-2020 | |
| 45 | Jerad Eickhoff | 29 | 2015-2021 | |
| 45 | Conor Fisk | 29 | 2019-2021 | |
| 45 | James Paxton# | 29 | 2014-2025 | |
| 45 | Erik Swanson# | 29 | 2019-2025 | |
| 45 | Jose Urena# | 29 | 2015-2025 | |
| 51 | Javier Assad# | 28 | 2023-2025 | |
| 51 | Vidal Nuno | 28 | 2013-2020 | |
| 51 | Johan Oviedo# | 28 | 2021-2025 | |
| 51 | Chris Rusin | 28 | 2013-2015 | |
| 51 | Trent Thornton# | 28 | 2018-2025 | |
| 56 | Jose Alvarez | 27 | 2015-2021 | |
| 56 | Tristan Beck# | 27 | 2021-2025 | |
| 56 | Ryan Feierabend | 27 | 2011-2021 | |
| 56 | Josh Fleming# | 27 | 2020-2025 | |
| 56 | Jeff Manship | 27 | 2013-2019 | |
| 56 | Adrian M. Martinez# | 27 | 2023-2025 | |
| 56 | Steve Matz# | 27 | 2015-2019 | |
| 56 | Joel Payamps# | 27 | 2019-2025 | |
| 56 | Jose A Ramirez | 27 | 2014-2019 | |
| 65 | Buddy Boshers | 26 | 2016-2021 | |
| 65 | Chris Hernandez | 26 | 2013-2016 | |
| 65 | Kolton Mahoney | 26 | 2020-2022 | |
| 65 | A.J. Puk# | 26 | 2019-2021 | |
| 65 | Matt Waldron# | 26 | 2022-2025 | |
| 65 | Spenser Watkins# | 26 | 2022-2025 | |
| 65 | Trevor Williams# | 26 | 2015-2024 | |
| 65 | Keaton Winn# | 26 | 2023-2025 | |
| 73 | David Buchanan# | 25 | 2015-2021 | |
| 73 | Derek Law# | 25 | 2016-2024 | |
| 73 | Matt Manning# | 25 | 2019-2023 | |
| 73 | Shairon Martis | 25 | 2013-2017 | |
| 73 | Tommy Romero# | 25 | 2022-2025 | |
| 73 | Matthew Tomshaw | 25 | 2017-2022 | |
| 73 | Kirby Yates# | 25 | 2014-2019 | |
| 80 | Albert Abreu# | 24 | 2016-2024 | |
| 80 | Christian Binford | 24 | 2017-2021 | |
| 80 | Archie Bradley | 24 | 2014-2016 | |
| 80 | Robbie Erlin# | 24 | 2013-2018 | |
| 80 | Drew Rucinski# | 24 | 2018-2025 | |
| 80 | Brady Singer# | 24 | 2020-2024 | |
| 80 | Chase Whitley | 24 | 2014-2019 | |
| 80 | Adam Wilk | 24 | 2014-2018 | |
| 88 | Tejay Antone# | 23 | 2020-2023 | |
| 88 | Shawn Armstrong# | 23 | 2017-2023 | |
| 88 | Manny Banuelos# | 23 | 2017-2024 | |
| 88 | Sean Gilmartin | 23 | 2017-2023 | |
| 88 | Ryan Helsley# | 23 | 2019-2022 | |
| 88 | Grant Holmes# | 23 | 2020-2025 | |
| 88 | James Hoyt | 23 | 2016-2021 | |
| 88 | Mickey Jannis | 23 | 2018-2022 | |
| 88 | Jason Jester | 23 | 2016-2021 | |
| 88 | Dinelson Lamet# | 23 | 2018-2025 | |
| 88 | Jacob Lopez# | 23 | 2023-2025 | |
| 88 | Ross Wolf | 23 | 2013-2016 | |
| 100 | Yadier Alvarez# | 22 | 2019-2025 |
