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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Cole Bellinger# | 20 | 2019-2023 | |
| 2 | Garrett Corthright | 18 | 2014-2017 | |
| 2 | Steven Gallardo | 18 | 2013-2021 | |
| 4 | Elias Pinales | 17 | 2013-2019 | |
| 4 | Jake Webb# | 17 | 2018-2023 | |
| 6 | Niall Windeler# | 16 | 2020-2023 | |
| 7 | Nicholas Hanson | 15 | 2013-2023 | |
| 8 | David Hurlbut | 14 | 2013-2019 | |
| 8 | Tayler Scott | 14 | 2013-2015 | |
| 10 | Brennan Bernardino# | 13 | 2016-2017 | |
| 10 | Joseph Krehbiel# | 13 | 2013-2015 | |
| 10 | Blake Loubier# | 13 | 2020-2023 | |
| 10 | Ryan Newell | 13 | 2013-2017 | |
| 10 | Tyler Pike# | 13 | 2013-2015 | |
| 10 | Radhames Quezada | 13 | 2013-2016 | |
| 10 | Max Roberts# | 13 | 2018-2021 | |
| 10 | Jared Robinson# | 13 | 2015-2018 | |
| 18 | Edwin Diaz# | 12 | 2013-2015 | |
| 18 | Chris Flexen# | 12 | 2013-2015 | |
| 18 | Justin Hooper# | 12 | 2020-2022 | |
| 18 | Kieran Lovegrove | 12 | 2014-2017 | |
| 22 | Zachary Bird# | 11 | 2013-2023 | |
| 22 | Juan Echevarria# | 11 | 2016-2023 | |
| 22 | Mitch Horacek | 11 | 2014-2016 | |
| 22 | Chih-Wei Hu# | 11 | 2014-2015 | |
| 22 | Keenan Kish | 11 | 2016-2017 | |
| 22 | Cody Kurz | 11 | 2013-2016 | |
| 22 | Nick Lee | 11 | 2013-2016 | |
| 22 | M.T. Minacci | 11 | 2016-2018 | |
| 22 | Mark Mixon# | 11 | 2020-2023 | |
| 22 | Eric Pardinho# | 11 | 2020-2023 | |
| 22 | Javier Reynoso | 11 | 2017-2022 | |
| 22 | Orlando Ribalta# | 11 | 2020-2023 | |
| 22 | Chris Vallimont# | 11 | 2019-2020 | |
| 22 | Zach Wolf# | 11 | 2020-2023 | |
| 22 | Max Wotell# | 11 | 2017-2023 | |
| 37 | Matt Ball | 10 | 2014-2017 | |
| 37 | Ryan Borucki# | 10 | 2013-2015 | |
| 37 | Michael Clevinger# | 10 | 2013-2014 | |
| 37 | Colton Cross | 10 | 2016-2018 | |
| 37 | Cédric De Grandpré# | 10 | 2023-2023 | |
| 37 | Adrian Houser# | 10 | 2013-2016 | |
| 37 | Ryne Inman# | 10 | 2017-2021 | |
| 37 | Pat Light | 10 | 2013-2015 | |
| 37 | Walker Lockett# | 10 | 2013-2016 | |
| 37 | Jairo Solis# | 10 | 2020-2021 | |
| 37 | Jake Stevenson# | 10 | 2020-2022 | |
| 48 | Diomenges Almengo | 9 | 2016-2020 | |
| 48 | Joe Broussard# | 9 | 2015-2016 | |
| 48 | Chase Chaney# | 9 | 2020-2023 | |
| 48 | Pat Connaughton | 9 | 2015-2019 | |
| 48 | Scott DeCecco | 9 | 2013-2015 | |
| 48 | Jeremiah Estrada# | 9 | 2019-2021 | |
| 48 | Bailey Falter# | 9 | 2016-2018 | |
| 48 | Jacob Forrester | 9 | 2020-2023 | |
| 48 | Tyler Garbee# | 9 | 2020-2022 | |
| 48 | Matt Gill# | 9 | 2020-2021 | |
| 48 | Luke Gillingham | 9 | 2018-2018 | |
| 48 | Scott Grist | 9 | 2016-2019 | |
| 48 | Stepan Havlicek | 9 | 2013-2022 | |
| 48 | Kyle Hinton# | 9 | 2021-2023 | |
| 48 | Zachary Jones | 9 | 2013-2015 | |
| 48 | Zachary Leigh# | 9 | 2022-2023 | |
| 48 | David Lucroy | 9 | 2016-2017 | |
| 48 | Mitch McKown | 9 | 2019-2023 | |
| 48 | Ryan McNeil# | 9 | 2013-2014 | |
| 48 | Craig Missigman | 9 | 2014-2017 | |
| 48 | Alexander Muren | 9 | 2013-2015 | |
| 48 | Daniel Nunan# | 9 | 2020-2022 | |
| 48 | Zach Quintana | 9 | 2013-2016 | |
| 48 | Grayson Rodriguez# | 9 | 2019-2023 | |
| 48 | Johnnie Schneider# | 9 | 2020-2022 | |
| 48 | David Sosebee | 9 | 2016-2022 | |
| 48 | Sean Sullivan# | 9 | 2022-2023 | |
| 48 | Kyle Twomey | 9 | 2016-2017 | |
| 48 | Zakery Wasilewski | 9 | 2013-2016 | |
| 77 | Jacob Blank# | 8 | 2019-2021 | |
| 77 | Logan Boyd | 8 | 2016-2017 | |
| 77 | Garrison Bryant# | 8 | 2018-2020 | |
| 77 | Brock Burke# | 8 | 2015-2018 | |
| 77 | Dakody Clemmer# | 8 | 2017-2023 | |
| 77 | Zachary Correll# | 8 | 2016-2016 | |
| 77 | Kevin Coulter# | 8 | 2020-2021 | |
| 77 | Derek De Young | 8 | 2013-2015 | |
| 77 | Brock Dykxhoorn | 8 | 2017-2020 | |
| 77 | Scott Effross# | 8 | 2016-2018 | |
| 77 | Evan Estes# | 8 | 2019-2021 | |
| 77 | Andrew Ferreira | 8 | 2013-2015 | |
| 77 | Conor Fisk# | 8 | 2016-2017 | |
| 77 | A.J. Franklin | 8 | 2020-2020 | |
| 77 | Kody Funderburk# | 8 | 2019-2019 | |
| 77 | Lucas Giolito# | 8 | 2013-2015 | |
| 77 | Joey Gonzalez# | 8 | 2019-2023 | |
| 77 | Scott Griggs | 8 | 2013-2016 | |
| 77 | Ben Gross# | 8 | 2020-2021 | |
| 77 | Anthony Guardado# | 8 | 2016-2018 | |
| 77 | Bradley Hanner# | 8 | 2020-2022 | |
| 77 | Nicholas Johnson# | 8 | 2019-2023 | |
| 77 | Kyle Jones# | 8 | 2023-2023 | |
| 77 | Sam Keating# | 8 | 2019-2021 |
