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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Luis Ríos# | 7 | 2027-2030 | |
| 2 | David Henderson | 6 | 2016-2025 | |
| 2 | Nobuo Yamashita# | 6 | 2025-2030 | |
| 4 | Manuel García | 5 | 2014-2021 | |
| 4 | Gregg Wagner | 5 | 2019-2028 | |
| 4 | Chris West# | 5 | 2020-2027 | |
| 7 | Jack MacAsgill# | 4 | 2023-2029 | |
| 7 | José Ramírez | 4 | 2015-2019 | |
| 9 | Ramón Rivera# | 3 | 2023-2028 | |
| 9 | Cale Sutton# | 3 | 2015-2030 | |
| 11 | Gabriel Pérez# | 2 | 2023-2028 | |
| 11 | Ramiro Salazar | 2 | 2016-2027 | |
| 13 | John Farrell | 1 | 2016-2022 | |
| 13 | Tommy Jones# | 1 | 2015-2030 | |
| 13 | António Pérez# | 1 | 2021-2030 | |
| 16 | Jay Parker# | 0 | 2024-2028 |
