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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Nick Bradley | .3161 | 2005-2011 | |
| 2 | Chuck Smith | .3225 | 2008-2016 | |
| 3 | Denis Boucher | .3263 | 1992-2003 | |
| 4 | Joaquin Benoit | .3378 | 2001-2012 | |
| 5 | Frank Edwards | .3389 | 2010-2022 | |
| 6 | Denny Bautista | .3394 | 2005-2015 | |
| 7 | Tim Redding | .3429 | 2001-2016 | |
| 8 | Dave Coggin | .3455 | 2002-2010 | |
| 9 | Eduardo Ruíz | .3465 | 2015-2025 | |
| 10 | Ken Smith | .3498 | 2000-2006 | |
| 11 | Roger Salkeld | .3552 | 1993-2006 | |
| 11 | Jeff Haley | .3552 | 2007-2020 | |
| 13 | Lee Rice | .3563 | 2000-2009 | |
| 14 | Ned Ames | .3582 | 2012-2023 | |
| 15 | Enrique Guerrero | .3599 | 2006-2012 | |
| 16 | Kyle Lohse | .3625 | 2001-2014 | |
| 16 | John Lannan | .3625 | 2011-2020 | |
| 18 | Kevin Robinson | .3639 | 2009-2022 | |
| 19 | Floyd Johnston | .3651 | 2005-2012 | |
| 20 | Derek Duffy | .3667 | 2002-2013 | |
| 21 | Steve Hayes | .3668 | 2014-2022 | |
| 22 | Jerome Williams | .3669 | 2003-2016 | |
| 23 | Wayne McDaniel | .3670 | 2009-2018 | |
| 24 | Luis Marino | .3695 | 2005-2012 | |
| 25 | José Tañón | .3710 | 2001-2011 | |
| 26 | Alfredo Guerrero | .3725 | 2003-2012 | |
| 27 | Jose Valverde | .3731 | 2003-2017 | |
| 28 | Jim Parque | .3732 | 1998-2010 | |
| 29 | Scott Eyre | .3750 | 1999-2008 | |
| 30 | Dan C Smith | .3773 | 1999-2005 | |
| 31 | Scott Downs | .3776 | 2000-2013 | |
| 32 | António González | .3783 | 2007-2021 | |
| 33 | Alan Reynolds | .3817 | 2000-2013 | |
| 34 | Mike Wood | .3841 | 2005-2014 | |
| 35 | Keith Compton | .3843 | 2002-2011 | |
| 36 | Kyle Dawson | .3857 | 2010-2017 | |
| 37 | Leonardo Rodríguez | .3859 | 2001-2013 | |
| 38 | Paul Williams | .3871 | 2012-2026 | |
| 39 | P.J. Fortier | .3876 | 2003-2012 | |
| 39 | Daisuke Matsuzaka | .3876 | 2010-2023 | |
| 41 | Larry Sherman | .3880 | 2002-2010 | |
| 42 | Jeremy Guthrie | .3881 | 2006-2017 | |
| 43 | Kevin Chamberlain | .3896 | 2002-2011 | |
| 44 | Brandon Lyon | .3897 | 2001-2011 | |
| 45 | Juan Rivera | .3902 | 2002-2010 | |
| 46 | Jaime Garza | .3903 | 2002-2008 | |
| 47 | Steven Miller | .3905 | 2018-2029 | |
| 48 | Jason Johnson | .3912 | 1997-2008 | |
| 49 | Chris C George | .3913 | 2001-2014 | |
| 49 | Curt Cameron | .3913 | 2000-2011 | |
| 51 | Cody Wade | .3919 | 2009-2019 | |
| 52 | Filiberto Bolzoni | .3923 | 2002-2007 | |
| 53 | John Roper | .3935 | 1994-2007 | |
| 53 | Ken Pittman | .3935 | 2013-2024 | |
| 53 | Dan McAllister | .3935 | 2016-2028 | |
| 56 | Haywood Horn | .3939 | 2003-2015 | |
| 57 | Mike Bannon | .3943 | 2003-2014 | |
| 58 | Joey Wells | .3950 | 2003-2011 | |
| 58 | Andrés Silva | .3950 | 2014-2025 | |
| 60 | Pablo Torres | .3953 | 2000-2009 | |
| 61 | Byron Guffin | .3994 | 2010-2022 | |
| 62 | James Shields | .4010 | 2008-2019 | |
| 63 | Mike Leake | .4020 | 2011-2024 | |
| 64 | Sean Lee | .4021 | 2012-2022 | |
| 65 | Alfredo Aceves | .4022 | 2014-2020 | |
| 66 | Markus Schmidt | .4023 | 2003-2013 | |
| 67 | Jason Dickson | .4024 | 1996-2006 | |
| 68 | Matt Garza | .4033 | 2008-2018 | |
| 69 | Héctor García | .4037 | 2002-2011 | |
| 70 | Jason Williams | .4053 | 2014-2024 | |
| 71 | Mike Jordan | .4055 | 2007-2014 | |
| 72 | Rob Dixon | .4077 | 2002-2016 | |
| 73 | David Rodríguez | .4078 | 2000-2009 | |
| 74 | Steven Holroyd | .4087 | 2013-2027 | |
| 75 | Tony McKnight | .4095 | 2000-2009 | |
| 76 | Doug Ball | .4099 | 2007-2021 | |
| 77 | Shawn Sedlacek | .4106 | 2002-2014 | |
| 78 | Phil Barnes | .4128 | 2009-2020 | |
| 79 | Nate Cornejo | .4140 | 2002-2011 | |
| 80 | Willie Parker | .4143 | 2003-2015 | |
| 81 | Eric Brennan# | .4147 | 2023-2031 | |
| 82 | Ray Lucas | .4149 | 2002-2011 | |
| 83 | Armando Galarraga | .4158 | 2009-2021 | |
| 84 | Dave Buckner | .4179 | 2002-2010 | |
| 85 | Blake Thompson | .4180 | 2003-2009 | |
| 86 | Rob Patterson | .4182 | 2002-2012 | |
| 87 | Wilbur Andrews | .4184 | 2018-2030 | |
| 88 | Sugita Shirai# | .4200 | 2025-2030 | |
| 89 | Chad Durbin | .4206 | 2001-2009 | |
| 90 | Louis Hamel | .4207 | 2000-2007 | |
| 91 | Veríssimo Hervedeiro | .4227 | 2004-2015 | |
| 92 | Jared Dawson | .4246 | 2016-2024 | |
| 93 | Dan Ainslie | .4287 | 2016-2027 | |
| 94 | Norman Taylor# | .4302 | 2022-2031 | |
| 95 | Terry Duffy | .4313 | 2009-2020 | |
| 96 | James Miller | .4314 | 2016-2024 | |
| 97 | Luke Prokopec | .4315 | 2000-2013 | |
| 98 | George Burke# | .4320 | 2017-2031 | |
| 99 | Tony Dotson# | .4336 | 2024-2031 | |
| 100 | Dan Middleton | .4338 | 2008-2018 |
