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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 | Nick Lockhart# | 18 | 2021-2025 | |
| 2 | Yankory Pimentel | 18 | 2016-2018 | |
| 5 | Travis Adams# | 15 | 2022-2024 | |
| 5 | Ryan Sherriff | 15 | 2013-2016 | |
| 5 | Ricky Vanasco# | 15 | 2018-2020 | |
| 8 | Tai Tiedemann | 14 | 2017-2022 | |
| 9 | Garrett Davila# | 13 | 2016-2026 | |
| 9 | Patrick Murphy# | 13 | 2014-2018 | |
| 11 | Julio Felix | 12 | 2013-2019 | |
| 11 | Seth Johnson# | 12 | 2020-2021 | |
| 11 | John King# | 12 | 2019-2020 | |
| 11 | Junior Mendez | 12 | 2014-2016 | |
| 11 | Jose Mesa Jr. | 12 | 2013-2017 | |
| 11 | Jeff Soptic | 12 | 2013-2016 | |
| 17 | Joe Barlow# | 11 | 2017-2018 | |
| 17 | Ty Buttrey# | 11 | 2013-2015 | |
| 17 | Caleb Frare | 11 | 2013-2015 | |
| 17 | Mike Gomez | 11 | 2015-2016 | |
| 17 | Michael Limoncelli# | 11 | 2020-2026 | |
| 17 | Logan Longwith | 11 | 2016-2018 | |
| 17 | Angel Macuare# | 11 | 2020-2021 | |
| 17 | Damien Magnifico | 11 | 2014-2015 | |
| 17 | Bryan Martinez | 11 | 2021-2023 | |
| 17 | Geordy Parra | 11 | 2015-2017 | |
| 17 | Erik Tolman# | 11 | 2022-2026 | |
| 28 | Trevor Belicek | 10 | 2017-2018 | |
| 28 | Mitch Brown | 10 | 2013-2014 | |
| 28 | Brad Case# | 10 | 2019-2026 | |
| 28 | Justin Crump | 10 | 2020-2025 | |
| 28 | Andrew Dalquist# | 10 | 2020-2024 | |
| 28 | Trey Dombroski# | 10 | 2024-2026 | |
| 28 | Edgar Gonzalez | 10 | 2022-2022 | |
| 28 | Quinton Low# | 10 | 2022-2025 | |
| 28 | Landen Maroudis# | 10 | 2024-2026 | |
| 28 | Gregorio Reyes# | 10 | 2020-2026 | |
| 28 | Erik Rivera# | 10 | 2021-2026 | |
| 28 | Sam Romero | 10 | 2020-2023 | |
| 28 | Nick Thwaits# | 10 | 2020-2026 | |
| 28 | Corey Walter | 10 | 2015-2016 | |
| 28 | Jonah Wesely | 10 | 2014-2017 | |
| 28 | Cole Wiper | 10 | 2014-2016 | |
| 44 | Yhoan Acosta | 9 | 2016-2018 | |
| 44 | Stiward Aquino# | 9 | 2021-2026 | |
| 44 | Aaron Bummer# | 9 | 2015-2017 | |
| 44 | Jimmy Burnette# | 9 | 2022-2026 | |
| 44 | Connor Coward | 9 | 2019-2019 | |
| 44 | Michael Flynn# | 9 | 2019-2026 | |
| 44 | Scott Frazier | 9 | 2014-2017 | |
| 44 | Cody Hacker | 9 | 2020-2022 | |
| 44 | Jagger Haynes# | 9 | 2022-2025 | |
| 44 | Stephen Jones# | 9 | 2021-2026 | |
| 44 | Danny Keller | 9 | 2013-2015 | |
| 44 | Austin Krob# | 9 | 2024-2024 | |
| 44 | Juan Pablo Lopez# | 9 | 2022-2025 | |
| 44 | Joseph Maher | 9 | 2013-2015 | |
| 44 | Gunner Mayer# | 9 | 2020-2026 | |
| 44 | Jaylen Nowlin# | 9 | 2022-2023 | |
| 44 | Pierson Ohl# | 9 | 2023-2023 | |
| 44 | Reese Olson# | 9 | 2020-2021 | |
| 44 | Jake Pfennigs# | 9 | 2023-2026 | |
| 44 | Julio Pinto | 9 | 2020-2023 | |
| 44 | Bodi Rascon# | 9 | 2022-2024 | |
| 44 | Luc Rennie | 9 | 2013-2015 | |
| 44 | Nash Walters# | 9 | 2017-2022 | |
| 44 | Trevor Williams# | 9 | 2014-2015 | |
| 44 | Tyler Willman | 9 | 2015-2020 | |
| 69 | Drew Beam# | 8 | 2025-2025 | |
| 69 | Matt Brash# | 8 | 2020-2021 | |
| 69 | Hever Bueno | 8 | 2017-2020 | |
| 69 | A.J. Burke | 8 | 2014-2016 | |
| 69 | Hyun-il Choi# | 8 | 2022-2025 | |
| 69 | Jacob Constante | 8 | 2013-2017 | |
| 69 | Jefferson Figueroa# | 8 | 2021-2024 | |
| 69 | Dalton Friend | 8 | 2013-2015 | |
| 69 | Hunter Hayes# | 8 | 2024-2026 | |
| 69 | Marc Iseneker | 8 | 2018-2018 | |
| 69 | Colton Johnson# | 8 | 2022-2026 | |
| 69 | Cory Jones | 8 | 2013-2015 | |
| 69 | Jacob Kostyshock | 8 | 2020-2024 | |
| 69 | Adam Maier# | 8 | 2023-2024 | |
| 69 | Sabier Marte# | 8 | 2025-2026 | |
| 69 | Zane Mills# | 8 | 2022-2026 | |
| 69 | Michael Morales# | 8 | 2022-2024 | |
| 69 | Mike Morin | 8 | 2013-2014 | |
| 69 | Austin Nicely | 8 | 2015-2016 | |
| 69 | Conner Nurse# | 8 | 2019-2025 | |
| 69 | Steven Okert# | 8 | 2013-2014 | |
| 69 | Kaleb Ort# | 8 | 2019-2025 | |
| 69 | Trent Palmer# | 8 | 2023-2026 | |
| 69 | Wesley Scott# | 8 | 2023-2024 | |
| 69 | Leif Strom# | 8 | 2020-2026 | |
| 69 | Jose Taveras | 8 | 2018-2023 | |
| 69 | Jose Torres | 8 | 2015-2016 | |
| 69 | Jose Valdez | 8 | 2013-2014 | |
| 69 | Shane Watson | 8 | 2013-2014 | |
| 98 | Ismael Aquino# | 7 | 2022-2026 | |
| 98 | Scott Barlow# | 7 | 2014-2016 | |
| 98 | Darren Bowen# | 7 | 2024-2025 |
