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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Manny Mesias | 7 | 2064-2067 | |
| 2 | Akil Baddoo | 4 | 2018-2027 | |
| 2 | Alejandro Guzman | 4 | 2033-2034 | |
| 2 | Toby Spack | 4 | 2030-2032 | |
| 5 | Fernando Akslen | 3 | 2070-2081 | |
| 5 | Carlos Encarnacion | 3 | 2029-2031 | |
| 5 | Jon Jackson | 3 | 2039-2040 | |
| 5 | Dan Kephart | 3 | 2057-2058 | |
| 5 | Alfredo Soto | 3 | 2064-2066 | |
| 10 | Lazaro Armenteros | 2 | 2018-2019 | |
| 10 | Ryan Cox | 2 | 2042-2043 | |
| 10 | Miguel Fernandez | 2 | 2051-2053 | |
| 10 | Beau Fuller# | 2 | 2086-2089 | |
| 10 | Vladimir Guerrero Jr. | 2 | 2017-2027 | |
| 10 | Mario Mora | 2 | 2067-2068 | |
| 10 | Tim Vaccaro | 2 | 2076-2079 | |
| 17 | Tony Capo | 1 | 2070-2077 | |
| 17 | Nick Elsner | 1 | 2060-2062 | |
| 17 | Beau Fenton# | 1 | 2094-2098 | |
| 17 | J.D. Gutierrez | 1 | 2068-2069 | |
| 17 | Nolan Miano | 1 | 2051-2055 | |
| 17 | Rory Randall | 1 | 2031-2032 | |
| 17 | Jim Redmond | 1 | 2032-2033 | |
| 17 | Tom Sleeper | 1 | 2086-2087 | |
| 25 | Josh Coney | 0 | 2037-2038 | |
| 25 | Mike Guerra | 0 | 2040-2056 | |
| 25 | Juan Inoa | 0 | 2028-2029 | |
| 25 | Pablo Rivera | 0 | 2057-2058 | |
| 25 | A.J. Thoma | 0 | 2058-2061 |
