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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | John Clayton | 14 | 2021-2023 | |
| 2 | Jim Dunleavy# | 9 | 2031-2036 | |
| 2 | Mike Lipide | 9 | 2027-2029 | |
| 4 | Hieronymus Bosch | 8 | 2025-2027 | |
| 4 | Milos Jaksch | 8 | 2028-2032 | |
| 4 | Andy Roarick# | 8 | 2031-2034 | |
| 7 | Mitchell Pate# | 7 | 2030-2036 | |
| 7 | Yaakov Shmerkin# | 7 | 2034-2037 | |
| 9 | Rubén Andrada | 6 | 2023-2025 | |
| 9 | Juan Romero | 6 | 2027-2029 | |
| 9 | Demeter Valverde | 6 | 2023-2024 | |
| 12 | Jin-yong Myung# | 5 | 2030-2032 | |
| 12 | Warren Willis | 5 | 2021-2025 | |
| 14 | Barton Nagel | 4 | 2022-2026 | |
| 14 | Luis Vicenteno | 4 | 2022-2023 | |
| 16 | Armaan Ebrahim | 3 | 2027-2028 | |
| 16 | Juan Jimínez# | 3 | 2028-2031 | |
| 16 | Warren King# | 3 | 2036-2037 | |
| 16 | Francisco Valentín | 3 | 2028-2030 | |
| 20 | Jorge Ayala | 1 | 2027-2030 | |
| 20 | Arturo Ballina | 1 | 2020-2023 | |
| 20 | Fred Burt | 1 | 2020-2024 | |
| 20 | Francisco Valentín | 1 | 2020-2022 |
