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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 | |
| 8 | Carlos Rodon# | 41 | 2016-2019 | |
| 8 | Drew Smyly# | 41 | 2013-2023 | |
| 10 | Dustin McGowan | 39 | 2014-2016 | |
| 10 | Marcus Walden | 39 | 2015-2023 | |
| 10 | Matt Wisler# | 39 | 2014-2019 | |
| 13 | Miguel A. Gonzalez | 38 | 2014-2018 | |
| 14 | Cory Gearrin | 37 | 2013-2020 | |
| 14 | Jorge Lopez# | 37 | 2015-2020 | |
| 14 | Andrew Suarez# | 37 | 2018-2022 | |
| 17 | Blake Beavan | 36 | 2013-2018 | |
| 17 | Nicholas Kingham# | 36 | 2016-2022 | |
| 19 | Aaron Brooks# | 34 | 2015-2023 | |
| 19 | Alex White | 34 | 2013-2017 | |
| 21 | Tyler Beede# | 33 | 2017-2023 | |
| 21 | Jake Thompson | 33 | 2016-2020 | |
| 23 | Anthony Cingrani# | 32 | 2013-2022 | |
| 23 | Cory Luebke | 32 | 2013-2016 | |
| 23 | Max Povse | 32 | 2018-2021 | |
| 23 | Andre Rienzo | 32 | 2013-2016 | |
| 23 | Tanner Roark | 32 | 2013-2016 | |
| 23 | Sal Romano# | 32 | 2017-2023 | |
| 29 | Austin Pruitt# | 31 | 2017-2022 | |
| 29 | Glenn Sparkman# | 31 | 2017-2023 | |
| 31 | Joe Gunkel# | 30 | 2018-2021 | |
| 31 | Daniel Mengden# | 30 | 2017-2023 | |
| 31 | Ross Ohlendorf | 30 | 2013-2016 | |
| 34 | Austin Adams | 29 | 2015-2020 | |
| 34 | Jerad Eickhoff# | 29 | 2015-2021 | |
| 34 | Conor Fisk# | 29 | 2019-2021 | |
| 34 | Asher Wojciechowski# | 29 | 2014-2023 | |
| 38 | Vidal Nuno | 28 | 2013-2020 | |
| 38 | Chris Rusin | 28 | 2013-2015 | |
| 40 | Jose Alvarez# | 27 | 2015-2021 | |
| 40 | Ryan Feierabend | 27 | 2011-2021 | |
| 40 | Daulton Jefferies# | 27 | 2020-2023 | |
| 40 | Jeff Manship | 27 | 2013-2019 | |
| 40 | Steve Matz# | 27 | 2015-2019 | |
| 40 | James Paxton# | 27 | 2014-2016 | |
| 40 | Adam Plutko# | 27 | 2017-2023 | |
| 40 | Jose A. Ramirez | 27 | 2014-2019 | |
| 40 | Alex Young# | 27 | 2017-2022 | |
| 40 | Rob Zastryzny# | 27 | 2018-2023 | |
| 50 | Buddy Boshers | 26 | 2016-2021 | |
| 50 | Chris Hernandez | 26 | 2013-2016 | |
| 50 | Kolton Mahoney# | 26 | 2020-2022 | |
| 50 | A.J. Puk# | 26 | 2019-2021 | |
| 50 | Cody Reed# | 26 | 2017-2019 | |
| 50 | Casey Sadler# | 26 | 2016-2023 | |
| 56 | David Buchanan# | 25 | 2015-2021 | |
| 56 | Kent Emanuel# | 25 | 2016-2020 | |
| 56 | Adrian Houser# | 25 | 2017-2020 | |
| 56 | Matt Manning# | 25 | 2019-2023 | |
| 56 | Shairon Martis | 25 | 2013-2017 | |
| 56 | Erik Swanson# | 25 | 2019-2022 | |
| 56 | Matthew Tomshaw | 25 | 2017-2022 | |
| 56 | Jose Urena# | 25 | 2015-2023 | |
| 56 | Kirby Yates# | 25 | 2014-2019 | |
| 65 | Christian Binford | 24 | 2017-2021 | |
| 65 | Archie Bradley# | 24 | 2014-2016 | |
| 65 | Robbie Erlin# | 24 | 2013-2018 | |
| 65 | Corey Oswalt# | 24 | 2018-2023 | |
| 65 | Johan Oviedo# | 24 | 2021-2023 | |
| 65 | Joel Payamps# | 24 | 2019-2023 | |
| 65 | Jacob Petricka | 24 | 2015-2022 | |
| 65 | Chase Whitley | 24 | 2014-2019 | |
| 65 | Adam Wilk | 24 | 2014-2018 | |
| 74 | Tejay Antone# | 23 | 2020-2023 | |
| 74 | Shawn Armstrong# | 23 | 2017-2023 | |
| 74 | Sean Gilmartin# | 23 | 2017-2023 | |
| 74 | Ryan Helsley# | 23 | 2019-2022 | |
| 74 | James Hoyt | 23 | 2016-2021 | |
| 74 | Mickey Jannis | 23 | 2018-2022 | |
| 74 | Jason Jester | 23 | 2016-2021 | |
| 74 | Ross Wolf | 23 | 2013-2016 | |
| 82 | Jake Barrett | 22 | 2014-2020 | |
| 82 | Dane Dunning# | 22 | 2019-2022 | |
| 82 | Luiz Gohara | 22 | 2018-2021 | |
| 82 | Cody Martin | 22 | 2015-2018 | |
| 82 | Casey Mize# | 22 | 2020-2022 | |
| 82 | Jon Moscot | 22 | 2015-2019 | |
| 82 | D.J. Myers# | 22 | 2020-2022 | |
| 82 | Luis Perdomo# | 22 | 2017-2018 | |
| 82 | Brooks Pounders | 22 | 2015-2020 | |
| 82 | Ricardo Sanchez# | 22 | 2019-2023 | |
| 82 | Nick Tropeano# | 22 | 2016-2023 | |
| 93 | Andrew Albers | 21 | 2014-2018 | |
| 93 | Yadier Alvarez# | 21 | 2019-2023 | |
| 93 | Hiram Burgos | 21 | 2014-2018 | |
| 93 | Daniel Corcino | 21 | 2014-2017 | |
| 93 | Braxton Garrett# | 21 | 2020-2023 | |
| 93 | Chad Kuhl# | 21 | 2017-2022 | |
| 93 | Seth Maness | 21 | 2014-2018 | |
| 93 | Alex Meyer | 21 | 2013-2017 |
