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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Rhett Wiseman# | 11 | 2018-2025 | |
| 2 | Michael Suchy | 6 | 2017-2019 | |
| 3 | Josh Almonte | 5 | 2014-2017 | |
| 4 | Mike Papi# | 3 | 2017-2024 | |
| 5 | Willie Abreu | 2 | 2019-2021 | |
| 5 | Preston Beck | 2 | 2016-2019 | |
| 5 | Niko Decolati# | 2 | 2019-2023 | |
| 5 | Johan Mieses# | 2 | 2018-2021 | |
| 5 | Jhailyn Ortiz# | 2 | 2018-2020 | |
| 10 | Zachary Esquerra | 1 | 2014-2016 | |
| 10 | Adonis Garcia | 1 | 2013-2016 | |
| 10 | Connor Oliver | 1 | 2014-2017 | |
| 10 | Daniel Pigott | 1 | 2016-2016 | |
| 10 | Brian Rey# | 1 | 2020-2021 | |
| 10 | Reed Rohlman | 1 | 2019-2022 | |
| 16 | John Andreoli# | 0 | 2013-2015 | |
| 16 | Tyler Esplin# | 0 | 2018-2024 | |
| 16 | Aaron Judge# | 0 | 2016-2016 |
