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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ray Bailey | 6 | 2033-2037 | |
| 1 | Justin Kiser# | 6 | 2054-2056 | |
| 1 | Roy McDaniel | 6 | 2018-2020 | |
| 1 | John Stewart# | 6 | 2050-2057 | |
| 5 | Shaun Sharp | 5 | 2021-2026 | |
| 5 | Joe White | 5 | 2039-2040 | |
| 7 | James Foley# | 4 | 2052-2056 | |
| 7 | Wes Salzberg# | 4 | 2054-2057 | |
| 9 | Byron Gill | 3 | 2038-2040 | |
| 9 | Alex Perez# | 3 | 2054-2057 | |
| 9 | Wil Ramos | 3 | 2038-2039 | |
| 9 | Matt Redd# | 3 | 2051-2053 | |
| 13 | Victor Badillo# | 2 | 2050-2055 | |
| 13 | Andreas Kubel | 2 | 2028-2029 | |
| 13 | Lorenzo Rosado# | 2 | 2055-2057 | |
| 16 | Oscar Dones# | 1 | 2047-2049 | |
| 16 | Tokuma Eida | 1 | 2021-2024 | |
| 16 | Joe Kennedy | 1 | 2016-2017 | |
| 19 | Ron Acker | 0 | 2016-2026 | |
| 19 | Tetsu Araki | 0 | 2017-2025 | |
| 19 | Austin Dodds | 0 | 2038-2040 | |
| 19 | Andy Pope | 0 | 2046-2048 |
