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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Noah Davis# | 19 | 2020-2022 | |
| 2 | Justin Jarvis# | 18 | 2019-2022 | |
| 2 | Yankory Pimentel | 18 | 2016-2018 | |
| 4 | Ryan Sherriff# | 15 | 2013-2016 | |
| 4 | Ricky Vanasco# | 15 | 2018-2020 | |
| 6 | Tai Tiedemann# | 14 | 2017-2022 | |
| 7 | Patrick Murphy# | 13 | 2014-2018 | |
| 8 | Julio Felix | 12 | 2013-2019 | |
| 8 | Luis D. Garcia# | 12 | 2020-2023 | |
| 8 | Seth Johnson# | 12 | 2020-2021 | |
| 8 | John King# | 12 | 2019-2020 | |
| 8 | Junior Mendez | 12 | 2014-2016 | |
| 8 | Jose Mesa Jr.# | 12 | 2013-2017 | |
| 8 | Jeff Soptic | 12 | 2013-2016 | |
| 15 | Joe Barlow# | 11 | 2017-2018 | |
| 15 | Ty Buttrey# | 11 | 2013-2015 | |
| 15 | Garrett Davila# | 11 | 2016-2018 | |
| 15 | Kevin Dickey# | 11 | 2020-2023 | |
| 15 | Caleb Frare | 11 | 2013-2015 | |
| 15 | Mike Gomez | 11 | 2015-2016 | |
| 15 | Logan Longwith | 11 | 2016-2018 | |
| 15 | Angel Macuare# | 11 | 2020-2021 | |
| 15 | Damien Magnifico | 11 | 2014-2015 | |
| 15 | Bryan Martinez# | 11 | 2021-2023 | |
| 15 | Keury Mella# | 11 | 2014-2015 | |
| 15 | Geordy Parra | 11 | 2015-2017 | |
| 27 | Travis Adams# | 10 | 2022-2023 | |
| 27 | Trevor Belicek | 10 | 2017-2018 | |
| 27 | Nick Bennett# | 10 | 2020-2021 | |
| 27 | Mitch Brown | 10 | 2013-2014 | |
| 27 | Andrew Dalquist# | 10 | 2020-2022 | |
| 27 | Edgar Gonzalez# | 10 | 2022-2022 | |
| 27 | Nick Lockhart# | 10 | 2021-2023 | |
| 27 | Erik Rivera# | 10 | 2021-2023 | |
| 27 | Sam Romero | 10 | 2020-2023 | |
| 27 | Corey Walter | 10 | 2015-2016 | |
| 27 | Jonah Wesely | 10 | 2014-2017 | |
| 27 | Cole Wiper | 10 | 2014-2016 | |
| 39 | Yhoan Acosta# | 9 | 2016-2018 | |
| 39 | Tomas Alastre# | 9 | 2022-2023 | |
| 39 | C.J. Broussard# | 9 | 2018-2023 | |
| 39 | Aaron Bummer# | 9 | 2015-2017 | |
| 39 | Brad Case# | 9 | 2019-2020 | |
| 39 | Connor Coward# | 9 | 2019-2019 | |
| 39 | Scott Frazier | 9 | 2014-2017 | |
| 39 | Cody Hacker# | 9 | 2020-2022 | |
| 39 | Damon Jones# | 9 | 2018-2019 | |
| 39 | Stephen Jones# | 9 | 2021-2023 | |
| 39 | Danny Keller | 9 | 2013-2015 | |
| 39 | Joseph Maher | 9 | 2013-2015 | |
| 39 | Jaylen Nowlin# | 9 | 2022-2023 | |
| 39 | Pierson Ohl# | 9 | 2023-2023 | |
| 39 | Reese Olson# | 9 | 2020-2021 | |
| 39 | Julio Pinto | 9 | 2020-2023 | |
| 39 | Luc Rennie | 9 | 2013-2015 | |
| 39 | Nash Walters# | 9 | 2017-2022 | |
| 39 | Trevor Williams# | 9 | 2014-2015 | |
| 39 | Tyler Willman | 9 | 2015-2020 | |
| 59 | Matt Brash# | 8 | 2020-2021 | |
| 59 | Hever Bueno# | 8 | 2017-2020 | |
| 59 | A.J. Burke | 8 | 2014-2016 | |
| 59 | Hyun-il Choi# | 8 | 2022-2023 | |
| 59 | Jacob Constante | 8 | 2013-2017 | |
| 59 | Gabriel Cotto# | 8 | 2020-2021 | |
| 59 | Justin Crump# | 8 | 2020-2023 | |
| 59 | Jefferson Figueroa# | 8 | 2021-2023 | |
| 59 | Michael Flynn# | 8 | 2019-2020 | |
| 59 | Dalton Friend | 8 | 2013-2015 | |
| 59 | Chris Holba# | 8 | 2023-2023 | |
| 59 | Marc Iseneker | 8 | 2018-2018 | |
| 59 | Cory Jones | 8 | 2013-2015 | |
| 59 | Peyton Miller# | 8 | 2020-2023 | |
| 59 | Mike Morin | 8 | 2013-2014 | |
| 59 | Austin Nicely | 8 | 2015-2016 | |
| 59 | Conner Nurse# | 8 | 2019-2022 | |
| 59 | Steven Okert# | 8 | 2013-2014 | |
| 59 | Nick Snyder# | 8 | 2018-2021 | |
| 59 | Jose Taveras | 8 | 2018-2023 | |
| 59 | Jose Torres | 8 | 2015-2016 | |
| 59 | Jose Valdez | 8 | 2013-2014 | |
| 59 | Shane Watson | 8 | 2013-2014 | |
| 82 | Scott Barlow# | 7 | 2014-2016 | |
| 82 | Gerson Bautista# | 7 | 2016-2017 | |
| 82 | Connor Berry# | 7 | 2020-2023 | |
| 82 | Tanner Bushue | 7 | 2013-2016 | |
| 82 | Ethan Clark | 7 | 2016-2018 | |
| 82 | Adrian Del Moral# | 7 | 2020-2022 | |
| 82 | Luis Heredia | 7 | 2013-2013 | |
| 82 | Adam Hill# | 7 | 2019-2021 | |
| 82 | Leonard Hollins | 7 | 2013-2016 | |
| 82 | Clinton Hollon | 7 | 2015-2017 | |
| 82 | Jason Hoppe | 7 | 2015-2016 | |
| 82 | Lucas Lanphere | 7 | 2014-2017 | |
| 82 | Conor Larkin# | 7 | 2022-2023 | |
| 82 | Kyle Leahy# | 7 | 2022-2022 | |
| 82 | Evan Lumbert | 7 | 2020-2023 | |
| 82 | Shane McCarthy# | 7 | 2019-2021 | |
| 82 | Alec Mills# | 7 | 2013-2013 | |
| 82 | Michael Morales# | 7 | 2022-2023 | |
| 82 | Jacob Morris | 7 | 2016-2019 |
