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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jon Osterman# | 10 | 2028-2033 | |
| 2 | Luis Ríos# | 9 | 2027-2033 | |
| 3 | Ralph Cranford# | 7 | 2030-2033 | |
| 3 | Nobuo Yamashita# | 7 | 2025-2032 | |
| 5 | David Henderson | 6 | 2016-2025 | |
| 6 | Manuel García | 5 | 2014-2021 | |
| 6 | Gregg Wagner | 5 | 2019-2028 | |
| 6 | Chris West | 5 | 2020-2027 | |
| 9 | Jack MacAsgill | 4 | 2023-2029 | |
| 9 | José Ramírez | 4 | 2015-2019 | |
| 11 | Count Dante# | 3 | 2025-2033 | |
| 11 | Ramón Rivera# | 3 | 2023-2028 | |
| 11 | Cale Sutton | 3 | 2015-2031 | |
| 14 | Gabriel Pérez# | 2 | 2023-2028 | |
| 14 | Ramiro Salazar | 2 | 2016-2027 | |
| 16 | John Farrell | 1 | 2016-2022 | |
| 16 | Tommy Jones# | 1 | 2015-2033 | |
| 16 | António Pérez# | 1 | 2021-2032 | |
| 16 | Julián Salcido# | 1 | 2027-2032 | |
| 20 | Jay Parker# | 0 | 2024-2028 |
