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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Thad Green# | 33 | 2019-2022 | |
| 2 | Myles Thomas# | 30 | 2019-2024 | |
| 3 | Michael Sasse# | 25 | 2021-2023 | |
| 4 | David Daniels# | 24 | 2019-2023 | |
| 4 | Adrian Houser# | 24 | 2013-2014 | |
| 4 | Burt Walters# | 24 | 2019-2022 | |
| 7 | Mike Flint# | 23 | 2017-2021 | |
| 7 | Pete Smith# | 23 | 2019-2023 | |
| 9 | Steven Jennings# | 22 | 2020-2023 | |
| 9 | Guillermo Polanco# | 22 | 2018-2022 | |
| 11 | Francis Burns# | 21 | 2019-2023 | |
| 11 | Jack Miller# | 21 | 2021-2022 | |
| 13 | Hudson Boyd# | 20 | 2013-2014 | |
| 13 | Nolan Sanburn# | 20 | 2015-2023 | |
| 15 | Eduardo Aldama | 19 | 2012-2014 | |
| 15 | Joel Bender# | 19 | 2013-2023 | |
| 15 | Eduardo Fernández# | 19 | 2018-2018 | |
| 15 | António Pacheco | 19 | 2012-2017 | |
| 19 | Ralph Alexander | 18 | 2015-2016 | |
| 19 | Colten Brewer | 18 | 2012-2013 | |
| 19 | Lou Cooper# | 18 | 2019-2021 | |
| 19 | Robert Gilliam | 18 | 2012-2013 | |
| 19 | John Jenkins# | 18 | 2019-2023 | |
| 19 | Chris Marlowe | 18 | 2012-2016 | |
| 19 | Juan Méndez# | 18 | 2015-2018 | |
| 19 | Matt Rogers# | 18 | 2020-2021 | |
| 19 | Robert Stephenson# | 18 | 2012-2013 | |
| 19 | CJ Weins# | 18 | 2022-2023 | |
| 29 | Iván Encarnación# | 17 | 2017-2020 | |
| 29 | Tim James# | 17 | 2015-2017 | |
| 29 | Alex Moran# | 17 | 2020-2023 | |
| 29 | Nelson Navarro# | 17 | 2016-2017 | |
| 29 | Jacob Palisch# | 17 | 2022-2023 | |
| 29 | Miguel Reyna# | 17 | 2014-2018 | |
| 29 | Javier Rosado# | 17 | 2020-2022 | |
| 36 | Michael Allen# | 16 | 2018-2022 | |
| 36 | Chad Bryant# | 16 | 2019-2023 | |
| 36 | Drew Carpenter | 16 | 2020-2020 | |
| 36 | Bret Houchens# | 16 | 2017-2018 | |
| 36 | Chip Hunt# | 16 | 2019-2022 | |
| 36 | Tyler Matzek | 16 | 2013-2016 | |
| 36 | David McMichael# | 16 | 2018-2022 | |
| 36 | Marek Minarik# | 16 | 2013-2017 | |
| 36 | Joe Rush# | 16 | 2019-2022 | |
| 36 | José Santiago# | 16 | 2015-2016 | |
| 36 | Mike Shelton# | 16 | 2019-2024 | |
| 36 | Ben Trigueros# | 16 | 2019-2022 | |
| 36 | Hugues Vallone# | 16 | 2018-2020 | |
| 36 | Alberto Vega# | 16 | 2013-2014 | |
| 50 | Gary Adams# | 15 | 2020-2023 | |
| 50 | Johnny Bechtel# | 15 | 2019-2020 | |
| 50 | Billy Bishop# | 15 | 2017-2023 | |
| 50 | Don Fier# | 15 | 2018-2023 | |
| 50 | Tyler Glasnow# | 15 | 2012-2016 | |
| 50 | Christian Graham# | 15 | 2019-2020 | |
| 50 | Carlos Gómez# | 15 | 2022-2023 | |
| 50 | Mike Hogan# | 15 | 2019-2023 | |
| 50 | Seth Johnson# | 15 | 2020-2021 | |
| 50 | Carlos Juárez# | 15 | 2019-2022 | |
| 50 | Nicholas Kingham# | 15 | 2012-2012 | |
| 50 | Paul Larsen# | 15 | 2020-2023 | |
| 50 | Christopher Lee# | 15 | 2013-2014 | |
| 50 | Félix López# | 15 | 2018-2021 | |
| 50 | Keith Malone# | 15 | 2019-2021 | |
| 50 | Jacob Maton# | 15 | 2022-2023 | |
| 50 | Roberto Padilla | 15 | 2012-2014 | |
| 50 | Bowman Sells# | 15 | 2023-2023 | |
| 50 | Henry Snyder# | 15 | 2020-2021 | |
| 50 | Skylar Spurrier# | 15 | 2018-2020 | |
| 50 | Daniel West# | 15 | 2021-2022 | |
| 50 | Charles Wright# | 15 | 2021-2022 | |
| 72 | Dan Allen# | 14 | 2017-2017 | |
| 72 | Jacob Beck# | 14 | 2019-2021 | |
| 72 | Austin Becker# | 14 | 2019-2020 | |
| 72 | George Clark# | 14 | 2018-2022 | |
| 72 | Max Duggan# | 14 | 2020-2022 | |
| 72 | Anthony Gordon# | 14 | 2022-2022 | |
| 72 | Stu Lilly# | 14 | 2016-2018 | |
| 72 | Reginald McMillan# | 14 | 2016-2017 | |
| 72 | Ray Moody# | 14 | 2018-2024 | |
| 72 | Paul Orr# | 14 | 2017-2017 | |
| 72 | Seaver Sheets# | 14 | 2020-2020 | |
| 72 | Cole Thompson# | 14 | 2019-2021 | |
| 72 | Dan Villari# | 14 | 2022-2023 | |
| 85 | Bryant Bachleitner# | 13 | 2020-2021 | |
| 85 | Cody Bradford# | 13 | 2023-2023 | |
| 85 | Eduardo Encarnación# | 13 | 2016-2017 | |
| 85 | Ethan Erickson# | 13 | 2021-2023 | |
| 85 | Alex Faedo# | 13 | 2017-2018 | |
| 85 | Dale Graves# | 13 | 2014-2015 | |
| 85 | Jonah Harris# | 13 | 2023-2023 | |
| 85 | Greg Hayes# | 13 | 2019-2020 | |
| 85 | Matt Lang# | 13 | 2017-2017 | |
| 85 | Jorge Martínez# | 13 | 2019-2022 | |
| 85 | Joe Pagán# | 13 | 2020-2021 | |
| 85 | José Pérez# | 13 | 2020-2021 | |
| 85 | Clarke Schmidt# | 13 | 2018-2019 | |
| 85 | Kevin Stone# | 13 | 2020-2022 | |
| 85 | Vincent Testaverde# | 13 | 2020-2023 | |
| 85 | Andry Ubiera# | 13 | 2012-2016 |
