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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Will May# | 18 | 2021-2024 | |
| 2 | Trey Dombroski# | 17 | 2022-2024 | |
| 2 | Juan Pérez# | 17 | 2019-2022 | |
| 4 | Tom Brandt# | 16 | 2019-2022 | |
| 5 | Bowman Sells# | 15 | 2019-2022 | |
| 6 | Manolo Barrón | 14 | 2015-2016 | |
| 6 | Mitch Carter | 14 | 2012-2014 | |
| 6 | Cade Fisher# | 14 | 2022-2024 | |
| 6 | Evan Shawver# | 14 | 2021-2024 | |
| 6 | Tristan Smith# | 14 | 2024-2025 | |
| 6 | Spencer Wojciechowski# | 14 | 2021-2022 | |
| 12 | Tanner Bailey# | 13 | 2023-2025 | |
| 12 | Parker Coil# | 13 | 2022-2025 | |
| 12 | Alex Early# | 13 | 2020-2021 | |
| 12 | Chayce McDermott# | 13 | 2022-2023 | |
| 12 | R.J. Scott# | 13 | 2020-2022 | |
| 17 | Anthony Gordon# | 12 | 2020-2021 | |
| 17 | Jorge Padilla | 12 | 2018-2021 | |
| 17 | Tom Robson# | 12 | 2012-2014 | |
| 17 | Max Wolff# | 12 | 2021-2024 | |
| 21 | Chris Catalon# | 11 | 2023-2025 | |
| 21 | Jorge García# | 11 | 2013-2016 | |
| 21 | Octávio Garza# | 11 | 2023-2025 | |
| 21 | Luis Guerra# | 11 | 2021-2022 | |
| 21 | Sergio Hernández# | 11 | 2021-2024 | |
| 21 | Miles Langhorne# | 11 | 2021-2023 | |
| 21 | Tyler Mattison# | 11 | 2020-2023 | |
| 21 | Parker McQuarrie# | 11 | 2019-2021 | |
| 21 | Júlio Rodríguez# | 11 | 2019-2021 | |
| 21 | Alejandro Rosário | 11 | 2015-2016 | |
| 21 | Carter Rustad# | 11 | 2023-2025 | |
| 21 | Colby Seeley# | 11 | 2021-2024 | |
| 21 | Ryan Zeferjahn# | 11 | 2019-2020 | |
| 34 | Joey Adams# | 10 | 2021-2021 | |
| 34 | Johnny Allen# | 10 | 2022-2025 | |
| 34 | John Baker# | 10 | 2020-2023 | |
| 34 | Julian Bosnic# | 10 | 2021-2022 | |
| 34 | Mike Clements# | 10 | 2019-2019 | |
| 34 | Ángelo González# | 10 | 2021-2023 | |
| 34 | Ryan Hilinski# | 10 | 2019-2020 | |
| 34 | Bradley Huggins# | 10 | 2021-2022 | |
| 34 | Ryan Jennings# | 10 | 2024-2025 | |
| 34 | Ben Kudrna# | 10 | 2021-2022 | |
| 34 | Tracy Mass# | 10 | 2015-2016 | |
| 34 | Gerardo Peña# | 10 | 2017-2020 | |
| 34 | Bill Poulin# | 10 | 2020-2022 | |
| 34 | Ryan Ramsey# | 10 | 2023-2025 | |
| 34 | Robbie Stewart# | 10 | 2021-2024 | |
| 34 | Mikey Tanner# | 10 | 2021-2024 | |
| 34 | Khalil Tate# | 10 | 2020-2022 | |
| 34 | Kent Wilson# | 10 | 2021-2024 | |
| 34 | Miguel Zambrano# | 10 | 2020-2022 | |
| 53 | Jacob Allen# | 9 | 2021-2022 | |
| 53 | Sergio Bernard# | 9 | 2012-2013 | |
| 53 | Jake Clemente# | 9 | 2024-2025 | |
| 53 | John Dwyer# | 9 | 2021-2024 | |
| 53 | Ethan Erickson# | 9 | 2019-2020 | |
| 53 | Mitch Farris# | 9 | 2024-2025 | |
| 53 | José Hernández# | 9 | 2017-2020 | |
| 53 | Jeriome Hill# | 9 | 2014-2015 | |
| 53 | Cody Hollingsworth# | 9 | 2021-2023 | |
| 53 | Mason Hope# | 9 | 2013-2013 | |
| 53 | Marcus Johnson# | 9 | 2022-2025 | |
| 53 | Ryan Lane# | 9 | 2020-2022 | |
| 53 | J.J. McCarthy# | 9 | 2020-2021 | |
| 53 | Quentin O'Dell# | 9 | 2021-2023 | |
| 53 | Connor O'Halloran# | 9 | 2025-2025 | |
| 53 | Tanner Pribble# | 9 | 2022-2023 | |
| 53 | Kyle Schroeder# | 9 | 2020-2023 | |
| 53 | Drew Scott# | 9 | 2022-2023 | |
| 53 | Hayden Sharp# | 9 | 2012-2013 | |
| 53 | Jimmy Shaw# | 9 | 2014-2016 | |
| 53 | Drew Swann# | 9 | 2023-2024 | |
| 53 | Jason Thornton# | 9 | 2019-2022 | |
| 53 | Scott Trevail# | 9 | 2015-2015 | |
| 53 | António Vega# | 9 | 2021-2024 | |
| 53 | Blake Walston# | 9 | 2020-2021 | |
| 78 | Jeremy Bond# | 8 | 2023-2025 | |
| 78 | Lucas Braun# | 8 | 2024-2025 | |
| 78 | Brian Brown# | 8 | 2020-2023 | |
| 78 | McCade Brown# | 8 | 2021-2022 | |
| 78 | Eric Cerantola# | 8 | 2021-2021 | |
| 78 | Kevin Cline# | 8 | 2021-2024 | |
| 78 | Hunter Cranton# | 8 | 2021-2023 | |
| 78 | Rhett Frank# | 8 | 2020-2021 | |
| 78 | Manuel García# | 8 | 2021-2022 | |
| 78 | Trey Gibson# | 8 | 2024-2025 | |
| 78 | Drew Gray# | 8 | 2022-2024 | |
| 78 | Matthew Greene# | 8 | 2023-2025 | |
| 78 | Edison Hall# | 8 | 2019-2021 | |
| 78 | Kevin Kellert# | 8 | 2024-2025 | |
| 78 | Maddox Kopp# | 8 | 2024-2024 | |
| 78 | Phil Madison# | 8 | 2019-2020 | |
| 78 | Jack Mahoney# | 8 | 2023-2023 | |
| 78 | Henry Morgan# | 8 | 2023-2024 | |
| 78 | Mark Moulin# | 8 | 2020-2022 | |
| 78 | Kevin Nicholas# | 8 | 2016-2016 | |
| 78 | Rafael Paz# | 8 | 2017-2018 | |
| 78 | Shawn Penny# | 8 | 2021-2024 | |
| 78 | Kyle Radatz# | 8 | 2016-2016 |
