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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | R.J. Manning* | .2668 | 2004-2019 | |
| 2 | Reynaldo Jimenez* | .2845 | 2002-2022 | |
| 3 | Shinji Yamashita | .2887 | 2004-2019 | |
| 4 | Ken Bayer* | .2954 | 1986-2004 | |
| 5 | Pat Bryant | .3012 | 1998-2016 | |
| 6 | Christian Vines | .3018 | 2040-2052 | |
| 7 | Andy Phillips | .3031 | 2042-2057 | |
| 8 | Jamie Gruell | .3040 | 2000-2016 | |
| 9 | Koichi Nakashima* | .3054 | 1995-2015 | |
| 10 | T.J. Mileski | .3076 | 2000-2015 | |
| 11 | Travis Oelschlager | .3110 | 1993-2009 | |
| 12 | Diego Lovera* | .3113 | 2010-2025 | |
| 13 | Pancho Herrera | .3130 | 1987-2002 | |
| 14 | Jerry Dean | .3134 | 1978-1984 | |
| 15 | Alejandro Portillo | .3163 | 2015-2029 | |
| 16 | Tom Kastner | .3176 | 2031-2047 | |
| 17 | Edgar Fajardo | .3186 | 2002-2022 | |
| 18 | Clarence Ortíz | .3188 | 1990-2006 | |
| 18 | Hans Gordinho | .3188 | 1991-2006 | |
| 20 | Joe Chavarraga* | .3234 | 1978-1987 | |
| 21 | Danny Rodriquez | .3241 | 1995-2009 | |
| 22 | Gil O'Moore* | .3244 | 1980-1996 | |
| 23 | Antonio Romo | .3245 | 2004-2018 | |
| 24 | Edgar Mejia* | .3257 | 2002-2016 | |
| 25 | J.J. Ballos | .3276 | 1999-2013 | |
| 26 | Mac Aaron | .3279 | 1990-2007 | |
| 27 | Dae-hee Yi | .3286 | 1988-2007 | |
| 28 | Basil Petrohilos | .3288 | 1991-2006 | |
| 29 | Dusty Casserino | .3289 | 2002-2019 | |
| 29 | Pat Dimmick* | .3289 | 1991-2005 | |
| 31 | Broderick Joyce | .3292 | 1978-1988 | |
| 32 | Adrián Díaz | .3296 | 1985-2005 | |
| 32 | Jamie Herberholz* | .3296 | 1998-2014 | |
| 34 | Ismael Ramírez | .3297 | 1995-2010 | |
| 35 | Pat Knight | .3309 | 1999-2017 | |
| 36 | Pat Yahn* | .3314 | 2007-2021 | |
| 37 | Rubén Pineda | .3320 | 1991-2006 | |
| 38 | Pat Evans* | .3325 | 2008-2024 | |
| 39 | Caden Hill | .3331 | 1987-2004 | |
| 40 | Robby Scriber | .3332 | 2007-2022 | |
| 41 | Tod Steffen# | .3340 | 2050-2060 | |
| 42 | Dusty Threatt | .3343 | 2016-2026 | |
| 43 | Edgar Salazar | .3350 | 1993-2014 | |
| 44 | Glen Jones | .3356 | 1990-2003 | |
| 44 | Colm Engle | .3356 | 1989-2004 | |
| 44 | Joe Aurillo* | .3356 | 1981-1995 | |
| 47 | Martin Carlton | .3360 | 1978-1991 | |
| 48 | Franklin Martinez | .3362 | 1994-2014 | |
| 49 | Yeong-suk Kang | .3369 | 1978-1988 | |
| 49 | Sheng Jong* | .3369 | 2031-2048 | |
| 51 | Derek Bell | .3370 | 2038-2051 | |
| 52 | Héctor Pagán | .3373 | 1989-2003 | |
| 53 | Eric Cafferty | .3375 | 1978-1988 | |
| 54 | David Rodriguez* | .3381 | 1999-2021 | |
| 55 | Tom Jensen | .3384 | 2025-2045 | |
| 56 | Víctor Rivera | .3387 | 1994-2008 | |
| 56 | Erik Pearsall | .3387 | 2008-2020 | |
| 58 | Tony Ramos* | .3388 | 2033-2047 | |
| 59 | Jonathon Burns | .3393 | 1999-2013 | |
| 59 | Wayne van Slyke | .3393 | 1978-1992 | |
| 59 | Kenshin Krsnich | .3393 | 1978-1993 | |
| 62 | Ethan Jackson | .3394 | 2025-2040 | |
| 63 | Doug Liggins | .3403 | 1978-1990 | |
| 64 | Dave Heath | .3409 | 1998-2006 | |
| 65 | Jerry Evans | .3412 | 1993-2009 | |
| 66 | Gus Jenkins | .3417 | 1992-2002 | |
| 66 | A.J. Ingle* | .3417 | 2018-2040 | |
| 68 | Felipe Vega | .3419 | 2004-2021 | |
| 69 | Donato Guardamagni* | .3421 | 1978-1995 | |
| 70 | Lorenzo Campos | .3423 | 2002-2012 | |
| 71 | Daniel Alvarez | .3429 | 1999-2013 | |
| 72 | Vernon Simmonds* | .3430 | 1978-1996 | |
| 73 | Oliver Lanham# | .3433 | 2053-2060 | |
| 74 | Tajo Delclos | .3434 | 1978-1990 | |
| 74 | Micah Wilson | .3434 | 2012-2026 | |
| 76 | Marco Perez | .3438 | 1999-2014 | |
| 76 | Shawn Mills | .3438 | 1987-2001 | |
| 78 | Jeff Franklin | .3439 | 1980-1990 | |
| 79 | Walter Lacour | .3442 | 1978-1984 | |
| 79 | Carl Pateshall | .3442 | 1978-1992 | |
| 81 | Tom Downs | .3448 | 1999-2011 | |
| 82 | Héctor Anaya | .3452 | 1991-2003 | |
| 83 | Dunmore Theodore* | .3456 | 1978-1994 | |
| 84 | Twymond Atif | .3457 | 2043-2056 | |
| 84 | Garret Clausnitzer | .3457 | 2029-2048 | |
| 86 | Ron Osborn | .3462 | 2015-2029 | |
| 87 | Joe O'Connelan | .3463 | 1978-1985 | |
| 88 | Ed Carroll* | .3465 | 2016-2032 | |
| 89 | Graham Hunter# | .3466 | 2044-2059 | |
| 89 | B.J. Swisher | .3466 | 2016-2029 | |
| 91 | Daniel Romero | .3468 | 1996-2013 | |
| 92 | Conan Wilkerson | .3469 | 1987-1997 | |
| 93 | Jesse VonEttingshausen | .3481 | 2000-2015 | |
| 94 | Travis Neal | .3496 | 2002-2014 | |
| 95 | Brendan Lindsey | .3497 | 2003-2015 | |
| 95 | Hisashi Tanaka | .3497 | 1998-2015 | |
| 97 | Doug Coates | .3502 | 1991-2004 | |
| 98 | Raúl Reyes | .3504 | 1989-2005 | |
| 99 | Pete Webster | .3506 | 1994-2006 | |
| 99 | Gil Brummett* | .3506 | 2006-2018 |
