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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Michael Morales# | 24 | 2023-2024 | |
| 2 | Juan Then# | 20 | 2021-2023 | |
| 3 | Gage Hinsz | 19 | 2024-2024 | |
| 3 | David Paulino | 19 | 2023-2023 | |
| 5 | Jaime Schultz | 18 | 2022-2024 | |
| 5 | Nick Travieso | 18 | 2024-2024 | |
| 7 | Justin Lopez# | 17 | 2023-2023 | |
| 8 | Calvin Ziegler# | 16 | 2023-2024 | |
| 9 | Jackson Cox# | 15 | 2023-2024 | |
| 9 | Yordanny Monegro# | 15 | 2024-2024 | |
| 11 | William Holmes | 14 | 2022-2023 | |
| 11 | Miguel Ullola# | 14 | 2022-2024 | |
| 11 | Jake Wong# | 14 | 2023-2023 | |
| 14 | Kristian Cardozo# | 13 | 2023-2024 | |
| 14 | Jerming Rosario# | 13 | 2022-2024 | |
| 16 | Ryan Webb# | 11 | 2023-2023 | |
| 17 | Irv Carter# | 10 | 2023-2023 | |
| 17 | Jorge Guzman# | 10 | 2023-2023 | |
| 17 | Cristian Hernandez# | 10 | 2022-2022 | |
| 20 | Yefri Del Rosario | 9 | 2021-2021 | |
| 20 | Micah Ottenbreit# | 9 | 2023-2023 | |
| 22 | Zack Erwin | 8 | 2023-2023 | |
| 22 | Gregory Santos# | 8 | 2023-2023 | |
| 22 | Brock Selvidge# | 8 | 2023-2023 | |
| 22 | Brady Smith# | 8 | 2024-2024 | |
| 26 | Mike Burrows# | 7 | 2021-2021 | |
| 26 | Victor Lizarraga# | 7 | 2023-2023 | |
| 26 | Brennan Malone# | 7 | 2022-2022 | |
| 26 | Adrian Morejon# | 7 | 2022-2022 | |
| 30 | Luis Gutierrez# | 6 | 2024-2024 | |
| 30 | DJ Herz# | 6 | 2022-2022 | |
| 30 | AJ Smith-Shawver# | 6 | 2023-2023 | |
| 30 | Josh Wolf# | 6 | 2023-2023 | |
| 34 | Drew Finley | 5 | 2024-2024 | |
| 34 | Elvis Garcia# | 5 | 2024-2024 | |
| 34 | Carlos Vargas# | 5 | 2021-2021 | |
| 37 | Junior Fernandez# | 4 | 2022-2022 | |
| 37 | Williams Jerez | 4 | 2022-2023 | |
| 37 | Esmerlin Vinicio# | 4 | 2023-2023 | |
| 37 | Jacob Zibin# | 4 | 2023-2023 | |
| 41 | Stiward Aquino | 3 | 2022-2023 | |
| 41 | Michael Braswell | 3 | 2023-2023 | |
| 41 | Alex McFarlane# | 3 | 2023-2023 | |
| 41 | Zander Mueth# | 3 | 2024-2024 | |
| 45 | Richard Gallardo# | 2 | 2022-2022 | |
| 45 | Josh James# | 2 | 2022-2022 | |
| 47 | Cristian Mena# | 1 | 2022-2022 |
