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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Austin Wilson | 17 | 2015-2018 | |
| 2 | Drew Mount# | 12 | 2022-2025 | |
| 3 | Drew Weeks | 11 | 2018-2021 | |
| 4 | Peyton Burdick# | 10 | 2022-2023 | |
| 4 | Jerar Encarnacion# | 10 | 2022-2025 | |
| 6 | Conner Capel# | 9 | 2020-2025 | |
| 6 | Ademar Rifaela | 9 | 2020-2022 | |
| 6 | Rubi Silva | 9 | 2013-2015 | |
| 9 | Stone Garrett# | 8 | 2019-2021 | |
| 10 | JJ Bleday# | 7 | 2021-2024 | |
| 10 | Mitch Haniger# | 7 | 2013-2014 | |
| 10 | Jordan Patterson | 7 | 2017-2021 | |
| 10 | Mitch Piatnik | 7 | 2019-2023 | |
| 14 | Forrestt Allday | 6 | 2014-2019 | |
| 14 | Javier Herrera | 6 | 2013-2018 | |
| 16 | Lane Adams | 5 | 2020-2021 | |
| 17 | Rymer Liriano | 4 | 2013-2022 | |
| 17 | Mike Yastrzemski# | 4 | 2018-2020 | |
| 19 | Juan C. Perez | 3 | 2013-2016 | |
| 19 | Brad Snyder | 3 | 2016-2018 | |
| 21 | Trey Harris# | 2 | 2020-2024 | |
| 21 | Drew Heid | 2 | 2013-2017 |
