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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Daniel García | 12 | 2026-2036 | |
| 1 | Tim Waters | 12 | 2026-2033 | |
| 3 | José Castillo | 11 | 2028-2033 | |
| 3 | Alfredo García | 11 | 2026-2031 | |
| 5 | Mike Russell | 10 | 2021-2025 | |
| 6 | Emery Miller | 9 | 2019-2025 | |
| 7 | Rand McNally | 7 | 2030-2034 | |
| 7 | Vladya Pugiev | 7 | 2032-2034 | |
| 7 | Geoff Rivers | 7 | 2026-2028 | |
| 10 | Mariano Juderías# | 6 | 2040-2041 | |
| 10 | Mare Riseley# | 6 | 2040-2042 | |
| 10 | Ken Watanabe | 6 | 2026-2029 | |
| 13 | Hani Azwan# | 5 | 2033-2039 | |
| 13 | Robert Hill | 5 | 2020-2027 | |
| 13 | Víctor López | 5 | 2026-2029 | |
| 16 | Edgardo De Jesús | 4 | 2030-2033 | |
| 16 | Jesús González | 4 | 2022-2033 | |
| 16 | Adrian McCoy | 4 | 2031-2033 | |
| 16 | James Pike | 4 | 2032-2040 | |
| 20 | Conor Gotaas# | 3 | 2038-2039 | |
| 20 | Michael Landry | 3 | 2023-2028 | |
| 20 | John Mayasich# | 3 | 2035-2041 | |
| 20 | Augusto Reyes# | 3 | 2037-2042 | |
| 24 | Travis Towns | 2 | 2035-2039 | |
| 25 | Bernardo Elías | 1 | 2021-2031 |
